Vacation Rentals By Owner In Osterville, MA

$790.38

Perfect Combination of Peace & Privacy - Close to Vibrant Village and Beach

Osterville, Massachusetts, United States

We love our new home! We chose the location because of its proximity to Cape Cod attractions!! The town of Osterville is 15 miles from the Sagamore Bridge leading to Cape Cod. Our home is 20 minutes from the Hyannis Port ferry to Nantucket and Martha's Vineyard. Mashpee Commons, an outdoor shopping/dining/movie destination, is a short 15 minute drive. If you like biking, the paths are abundant.brbrThe beaches are exceptional, and though there are several choices, we spend most of our time at Craigville Beach (10 minute drive) and Dowses Beach (7 minutes). These are perfect for families. A resident beach pass is provided to occupants. Joshua Pond beach is 4 minutes drive. The town of Osterville has great restaurant options, and unique shops.brbrThe home affords the combination of privacy and access to the town of Osterville. It is situated on over an acre of land, set back from the main road into town. There are sidewalks, if you choose to walk to town (under 2 miles). The front yard is perfect for lawn games, and the back yard has an outdoor kitchen which will enhance your stay. The indoor kitchen is ideal for those who like to cook, with gas range, double ovens, microwave, food processor, Breville air fryer, and Keurig coffee maker. I love the bar area which makes it fun for the cook to be a part of the fun!brbrThe home is elegantly appointed, with a first floor Master bedroom and a large screen smart TV. An additional King bedroom suite with full bath affords privacy and the 2 other bedrooms (Queen, and Full + Twin) have their own area in a separate wing of home. There are lovely places to read and relax.brbrA finished basement space for children to play gives everyone a chance to have time to themselves.brbrAnd, one word about the French Bakery (Amie) will not be enough!! They have prepared foods as well, and cooking classes, a true French experience right in heart of the Cape! So much to enjoy!

4

Bed

3

Bath

9

Sleeps

$221.09

/ Nightly

Private Vacation Home

2 Mi to Dowses Beach! Couples Haven in Osterville

Osterville, Massachusetts, United States

Welcome to your charming cottage retreat in Osterville, MA, where relaxation meets adventure on picturesque Cape Cod. Whether you're soaking up the sun, exploring the village charm, or simply unwinding by the firepit, this peaceful cottage offers the perfect blend of tranquility and coastal fun. Your unforgettable Cape Cod getaway starts here, book your stay today!brbr-- THE PROPERTY --brbrC0548270200brbrThe inviting outdoor space is perfect for making memories, featuring a furnished deck, patio with a firepit deal for evening gatherings under the stars. brbrInside, you'll find thoughtful amenities for comfort and convenience, including window A/C, WIFI access, streaming options like Netflix, fun board games, and a selection of books.brbr-- THE LOCATION --brbrJust a quick 5-minute drive to beautiful Dowses Beach and only a 2-minute walk to a swimmable freshwater pond, this cozy escape is ideal to enjoy coastal living.brbrSpend your days beachcombing along the shore, or teeing off at a scenic golf course just 15 minutes away. Take an easy 15-minute stroll into town to browse local shops, indulge in delicious restaurants, or pick up the essentials at the nearby market.brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-in

Bed

Bath

Sleeps

$750.32

/ Nightly

Private Vacation Home

Osterville Retreat – A/C, WiFi & Pet-Friendly

Osterville, Massachusetts, United States

4 Bedroom - 3.5 Baths - Sleeps 6brA 7-night Saturday-to-Saturday rental reservation is required during peak summer weeks. Many of our homes offer flexible stays with a 3 night minimum in the off season - ask our Reservation Specialists for more details.brComplimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish towels for total home occupancy.brWe offer a 4 pm Check-In and 10 am Check-Out brbrWelcome to 'O Captain! My Captain!' in the heart of Osterville. Short stroll to the beautiful Dowses beach, and downtown. This updated home is in a wonderful family-friendly neighborhood. Comfortable and spacious this 4 bedroom, 3.5 bath home has central A/C, WiFi and is dog friendly! Bonus linens and towels are included with this home.brbrOwners Share Why I Love My Home:brWe love to wake up early and sneak out to the deck for our morning coffee. As we sit in the lounge chairs and watch the countless chipmunks steal the birdseed from our beautiful family of cardinals, we simply enjoy the calm and quiet of our lovely cape cod mornings before heading to the beach. The outdoor shower is truly magical, please give it a try, it's life changing!! We hope you enjoy our home as much as we do! Welcome!brbrLet Us Tell You About This Home:brEnter this 4 bedroom, 3.5 bath home from the side door into the classic Cape Cod entryway. To the left is a relaxing open sitting area, and straight ahead a large eating nook with a built-in bench. Gorgeous white, state of the art, kitchen has everything you need to make fabulous meals plus a breakfast bar, a coffee station and even doggie bowls for the furry members of your family!br brHead down the hallway and find a half bath, Bedroom 1 with a queen tempurpedic sleeper sofa, and full bathroom with a stall shower. A family room with a TV (streaming only) and large comfy sectional couch with room for the whole family completes the first floor. br brFrom the living room, the fabulous lighthouse staircase will lead you to the second floor. Here you will find three cozy and relaxing bedrooms and two full bathrooms. One bath is located off the hall and the other is in the primary bedroom. brbrBedroom #2 has a full bed, closet, oversized bean bag, dresser and night table- Second floorbr brBedroom #3 has a full bed, closet, night stand, and dresser- Second floorbr brBedroom #4 has a king bed with Apple TV for streaming, night tables, desk with monitor, dresser and an ensuite full bathroom- Second floorbr brBack downstairs, off of the dining area, you will find sliders to the back deck with a table for outdoor dining, lounge chairs, and a private yard. Fire up the gas grill for dinner or jump in the enclosed outdoor shower after a sandy day at the beach. The yard is not fully fenced in. br brBeach parking pass is included with the property for 1 car at all Barnstable Beaches, including Dowses beach.brbrFree Tickets and Complimentary Activities! Create unforgettable memories and experience Cape Cod like a local! Enjoy $750 worth of daily exclusive free tickets to exciting local attractions through our partnership with Xplorie. Your amenities include activities such as Island Cruises, Whale Watch, Bike Rentals and admission to Whydah Pirate Museum. When you're not soaking up the sun on the beach, enjoy daily rounds of golf at Cranberry Valley or Chequessett Golf Courses and mini-golf for family fun.brbrWith all NEVR properties, we think of the little things to make your vacation special. Our Guest Welcome Bag, compliments of the homeowner, contains starter quantities of kitchen and bathroom essentials, with a few locally sourced snacks as well (subject to change based marketplace availability).brbrThis home offers Keyless Entry for your convenience.brNO SMOKING of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.brDOG FRIENDLY HOMES are for a DOG only. This home allows 1 dog with a $25 per night fee. With owner approval, a second dog may be considered for an additional $25 per night fee. A Pet Registration form must be completed upon reservation confirmation. brMax parking of cars at property: 3. No parking on lawn anytime brbrAdditional Information to Assist You:brDeparture cleaning is included with your reservation at no additional charge. Simply follow our basic check-out instructions at your departure. brState and local taxes are charged if applicable. brFor Reservations made over 60 days away, you will make two payments - 50% initial payment with reservation and the final balance will be auto billed to your credit card 60 days prior to arrival. We accept Mastercard and Visa for payments.brA confirmed reservation is non refundable--please consider purchasing trip cancellation insurance. Ask our guest specialist for more details regarding cancel options and trip insurance. br***Linens - bed sheets, bath/dish/beach towels and bath mats are included with this home but can be rented at time of booking or at a later date through our linen rental partner. Please ask our guest specialist for details. Our NEVR Homes come with mattress covers, pillows and a bed cover such as blanket, quilt, bedspread etc.brYou must be 25+ years old unless accompanied by a parent or guardian to book one of our Vacation Rental Homes. An ID must be furnished upon request. brbrArea Info: *Mileage is approximatebrbr0.8 mile to Dowses Beachbr0.9 mile to Main Streetbr Ice Creambr Restaurantsbr Coffee shopsbr3.6 miles to Craigville BeachbrbrDrive (6.4 miles) to Main Street Hyannis where you will find:brbrThe Steamship Authority FerrybrRestaurantsbrShoppingbrBarsbrBakeriesbrMuseumsbrGalleriesbr*Mileage is approximate

4

Bed

3

Bath

6

Sleeps

$855.93

/ Nightly

Private Vacation Home

The Cape Escape

Osterville, Massachusetts, United States

Welcome to your home away from home in Osterville, MA! This 2 bed, 2 bath home features a bonus room, in-ground pool, new hot tub, and sleeps 8 with a king bed, queen bed, queen sofa bed, and a new king hideabed in the living room. Enjoy a full kitchen, dining and living rooms, office/den, en suite main bedroom, 1st floor laundry, and included beach pass. Relax and make new memories in this spacious, centrally located getaway!brbrUpdated and welcoming home with spacious rooms and a lovely pool and deck to make being outside a fun priority. Back yard is fully fenced making it safe for a pup or the little people in your party.brbrPlease note that linens and bath and kitchen towels are provided. Beach towels are also provided. Sandy towels, etc are not allowed in the washer/ dryer. Pets are not allowed in the pool and should be kept off the beds.brbrDisclaimer: If a remote control is lost, you will be responsible for covering a replacement cost of $75, in addition to the cost of the remote itself.

Bed

Bath

Sleeps

$352.51

/ Nightly

Private Vacation Home

THREE BEDROOM CAPE NEAR PRIVATE SWIMMING POND

Osterville, Massachusetts, United States

Quiet three bedroom, two full bath Cape located on a dead-end street in the quaint town of Osterville.brFirst floor includes master queen bedroom with full bath, second bedroom with two twin bedsbr Also on first floor is second full bathroom, full equipped kitchen, dining room, and living room with sleeper sofa brSecond floor consists of kids room with two sets of bunk-beds, game table and computerbrCable TV's on both floors and Wireless Internet throughoutbrLaundry closet with washer and dryerbrSeparate air-conditioning in each roombrDeck with grill, table and chairsbrBeach Pass for ALL Barnstable Public and Private Beaches IncludedbrDog friendly rental- Additional fee Required brNon-smoking onlybrbr

Bed

Bath

Sleeps

$380.37

/ Nightly

Private Vacation Home

Osterville Gem Steps to Main St! Relax fireside

Osterville, Massachusetts, United States

2 Mi to Beach | Easy Access to Shops & Dining | Updated InteriorbrbrCraving a classic Cape Cod experience This 2-bed, 1-bath vacation rental in Osterville wraps cottage charm and coastal convenience into one inviting stay. It’s village living at its best — stroll to Main Street for your morning coffee, browse the local shops, or spend the day on Nantucket Sound. When you’re ready to recharge, the peaceful patio gives you a private retreat to pause and enjoy the Cape’s slower pace.brbr-- THE PROPERTY --brbrC0550080200brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 full bedbr- Bedroom 2: 1 bunk bed (twin/full)br- Living Room: 1 full sleeper sofabrbrCOTTAGE COMFORTSbr- Smart TV, fireplacebr- Dining tablebr- Private yard, picnic tablebr- Patio, gas grillbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Keurig (starter coffee provided)br- Toaster, microwavebr- Cooking basics, dishware & flatwarebrbrGENERALbr- Free WiFibr- Central A/C & heatingbr- Linens & towelsbrbrACCESSIBILITYbr- Single-story cottage, 3 steps to enterbrbrPARKINGbr- Parking space (1 vehicle)brbrADDT’L ACCOMMODATIONSbr- An additional property is available next door with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to bookingbrbr-- THE LOCATION --brbr- Easy access to uncrowded beaches & renowned Cape destinationsbr- Walk to Main Street: boutiques, art galleries & restaurantsbr- 1 mile to Nauticus Marinabr- 2 miles to Dowses Beachbr- 3 miles to Craigville Beachbr- 6 miles to Hyannisbr- 32 miles to Cape Cod National Seashorebr- 71 miles to Boston Logan Int'l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story cottage requires 3 steps to enter

Bed

Bath

Sleeps

$1342.5

/ Nightly

Private Vacation Home

Large waterfront home with deep water dock, you'll Fall in love with Breezy Bluff

Osterville, Massachusetts, United States

Waterfront-5BD, with bonus room-Deep Water Dock-Screen Porch-Close to Osterville Village-Beach Passbrbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy, from the guest book REVIEWS and more! * * * * brbrBreezy Bluff – Classic 5-Bedroom Cape with Deep Water Dock & Stunning Views of West Baybrbr**THIS PROPERTY IS AVAILABLE FOR 3 NIGHT RENTALS ALL SUMMER, WITH THE EXCEPTION OF THE WEEK OF THE 4TH OF JULY WEEK AND LABOR DAY WEEK**brbr*Deep water dock – bring your boat or rent one for the weekbr*Breathtaking Oyster Harbor views from almost every roombr*Screened-in sun porch with amazing viewsbr*Classic Sea Captain’s home filled with charmbr*Central air conditioning on first floor, window units upstairsbr*Landlord beach pass included – enjoy all Barnstable beachesbr*Walk to Osterville VillagebrbrStep into Breezy Bluff and experience a timeless Cape Cod retreat. The fully equipped kitchen with a center island welcomes you in, perfect for preparing meals for your group. Off the kitchen is a sunny bonus room with two twin beds, a desk, and a full bath with a shower—ideal for extra guests or as a quiet workspace.brbrThe dining room features a large table for gathering, while the spacious living room offers coastal décor, comfortable seating, and expansive windows showcasing stunning views.brbrOn the first floor, a queen bedroom awaits with a full bath featuring both a separate tub and shower.brbrUpstairs, all bedrooms are decorated in light coastal colors. The first bedroom has a king bed, water views, and an en-suite bathroom with a shower. The second bedroom offers a queen bed, bright and airy, while the third bedroom has two twin beds, perfect for kids. A shared full bathroom with a shower serves these rooms. The final upstairs bedroom includes a king bed (two twins pushed together) and beautiful water views—open the windows to feel the ocean breeze.brbrThe screened-in sun porch invites you to sip coffee or cocktails while watching the boats drift by. Outdoors, enjoy direct access to the private dock and the sparkling waters of West BaybrWest Bay leads to Nantucket SoundbrbrOsterville Village – 1 mile / 4-min drive, 20-min walk, 8-min bikebrDowses Beach – 2 miles / 6-min drive, 35-min walk, 12-min bikebrCraigville Beach – 4.5 miles / 12-min drive, 25-min bikebrMain Street Hyannis – 6 miles / 15-min drivebrHyannis Harbor & Ferries – 6.5 miles / 16-min drivebrMashpee Commons - 8.0 miles / 19- min drivebrbr**This home has a sister house right next door, thinking about a family reunion, birthday gathering or any special occasion rent both houses. **brbr**USAGE OF THE DOCK WILL REQUIRE TENANT TO NAME BREEZY BLUFF ON TENANTS LIABILITY POLICY, REFUNDABLE SECURITY DEPOSIT IS REQUIRED. AND APPROVAL OF THE BOAT FROM THE OWNER***brbr*** ASK ABOUT INFORMATION FOR LOCAL BOAT RENTAL COMPANIES***brbr***LINENS AND TOWELS INCLUDED,BEDS MADE***br***$500.00 CLEANING FEE***br***BEACH PASS INCLUDED***br***FREE WIFI***br ***SUNDAY TO SUNDAY ***br***NO SMOKING***br***DOGS CONSIDERED WITH OWNER'S APPROVAL AND FEES***br***Non Refundable $220.00 RESERVATION FEE;30 DAMAGE PROTECTION FEE;GUEST SERVICE FEE;APPLICABLE TAXESbrbr*****NIGHTLY RATES AVAILABLE, 3 NIGHT MINIMUM AND 600.00 CLEANING FEE***brbr ****FREE ACTIVITIES INCLUDED****brTo enhance your vacation experience, Kinlin Grover includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrClick the Xplorie button or visit the Free Activities page to see the free fun included with this Kinlin Grover rental! brbrAs a guest of Kinlin Grover, you'll receive free golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!brbrReviewsbrSubmit a Review for TMILLbr brSuperb!brReview Date: July 23, 2025brVacation Date: July 13, 2025brWe LOVED Breezy Bluff! Simple styling, perfectly in order with Cape vibe, that included everything & more. Lovely kitchen with big stand-around island, fabulous screen porch to read on for hours, convenient dock where our boat was instantly accesible, easy walk to town, parks & nearby Chart Room (priceless!). And the property manager and owner were so accommodating, without even asking. Can't wait to come back!brReviewed By: THCbr brTMILL – Very enjoyablebrReview Date: August 10, 2022brVacation Date: July 17, 2022brThis is a great place to spend time in the summer. Close to beaches but relaxing on the dock is just as good. Awesome place to bring a boat for sunset cruises, tubing, or heading out to the open ocean. Also very close to restaurants, shops, and of course, ice cream.brReviewed By: MFbrbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrKGC-TMILL

5

Bed

4

Bath

12

Sleeps

$4714.5

/ Nightly

Private Vacation Home

Luxury rental with pool. Close to village and beach RPMS157

Osterville, Massachusetts, United States

Michelle Sylvia luxury collection. Stunning Coastal Luxury in Osterville - 468 Wianno AvebrExperience Cape Cod living at its finest in this luxury home in Osterville Village. Perfectly positioned just a short stroll from Dowses Beach, this magnificent seaside home offers everything you need for an unforgettable stay. With six spacious bedrooms and six full baths, this property comfortably accommodates large groups, making it ideal for family gatherings or special getaways.brbrInside, the open-concept design seamlessly blends comfort with coastal elegance. Each bedroom is designed with relaxation in mind, and the six full baths provide ample convenience for all guests. Step outside to find a heated pool, perfect for enjoying sunny Cape Cod days, as well as a large yard for outdoor fun and entertaining.brBeyond the property, enjoy all that Osterville Village has to offer—quaint shops, delicious dining options, and beautiful beach days at nearby Dowses. Don’t miss this incredible chance to relax and recharge at an exceptional coastal retreat.brbrLuxury amenity of shampoo, body wash and conditioner in each bathroom and outdoor shower. brbrAll applicable taxes and fees apply.brbrBed sizes :brQueen first floorbrKingbrQueenbrKingbrQueenbr3 bunk beds

6

Bed

7

Bath

12

Sleeps

$393.45

/ Nightly

Private Vacation Home

Little Gem walking distance to Osterville Village

Osterville, Massachusetts, United States

Welcome to Your Ideal Vacation Rental in OstervillebrbrThis adorable property blends comfort, convenience, and coastal charm, ensuring a memorable and rejuvenating Cape Cod getaway.brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * 0brbr*Located in Osterville Villagebr*Walk to restaurants, shops, and marketsbr*Private deck,gas grill, yard, and enclosed outside showerbr*Beach pass includedbrbrStep inside to a bright, spacious living area furnished with stylish décor and a TV—perfect for relaxing after a day at the beach. The fully equipped kitchen has everything you need to prepare meals, whether it’s a quick breakfast before heading out or a sit-down dinner with family.brbrDown the hall are two inviting bedrooms designed for comfort and rest. The primary bedroom features a queen bed, while the second bedroom has two twin beds, accommodating up to four guests. A full bath completes the main living space.brbrOutdoors, enjoy your private deck and backyard. Sip your morning coffee in the sun, fire up the gas grill for an evening cookout, or rinse off in the enclosed outside shower after a day in the sun.brbrBedroom #1 Queen bed, Bedroom #2 Two twin bedsbrWindow AC in kitchenbrbr-Dowses Beach – 1 mile (4 min drive / 20 min walk / 6 min bike)br-Osterville Village shops & dining – 0.5 mile (2 min drive / 10 min walk / 3 min bike)br-Mashpee Commons – 7 miles (15 min drive)br-Hyannis Main Street & Harbor – 6 miles (15 min drive)br-Ferries to Nantucket & Martha’s Vineyard – 6 miles (15 min drive)brbr***ADDITIONAL FEES***br$200.00 CLEANING FEEbrLINENS AND TOWELS INCLUDED;BEDS MADEbrNO PETS ALLOWEDbr$220 NON-REFUNDABLE RESERVATION FEE;$30 DAMAGE PROTECTION FEE;GUEST SERVICE FEE;ALL APPLICABLE TAXESbrNO SMOKINGbrSATURDAY TO SATURDAY RENTALbrFREE WIFIbrbr****FREE ACTIVITIES INCLUDED****brTo enhance your vacation experience, Kinlin Grover includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrClick the Xplorie button or visit the Free Activities page to see the free fun included with this Kinlin Grover rental! brbrAs a guest of Kinlin Grover, you'll receive free golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrbrKGC-TGRIFF

Bed

Bath

Sleeps

$5605.22

/ Nightly

Private Vacation Home

The Ultimate Cape Cod luxury home. Dock, pool, hot tub and views! RPMS104

Osterville, Massachusetts, United States

Michelle Sylvia high end Luxury collection rental home. Welcome to Osterville! This spacious newly renovated rental property is located in the gated community of Oyster Harbors with a heated infinity pool, hot tub and spectacular water views of West Bay with a private dock. Drink your coffee on the terrace, enjoy the views or relax in the hot tub. Make plans to take your boat out for the day to nearby Sampson's Island. brbrThis property has all you could desire in a Cape Cod retreat: private, gated island community, over 6,000 square feet of luxury living in this Cape Cod estate. There are six bedrooms including two bedrooms on the first floor, one being a primary suite. Not far from Dowses Beach and all Osterville village has to offer. Dock has approval for a 29 foot boat with a 4 foot draft Dock has a float. brBed sizes:brKing primary suite [ Full bath ] First floorbrKing first floor with bath [ shower ]brSecond floor:brKingbr2 queens Jack and Jill bath brKingbrOver garage area has full bath and large room with 2 queen and 2 twinbrbrAll applicable taxes and fees apply.

Bed

Bath

Sleeps

$3094.66

/ Nightly

Private Vacation Home

Waterfront Estate in Prestigious Osterville | Private Beach, Pool & Hot Tub and Central AC-Sleeps 15

Osterville, Massachusetts, United States

Waterfront Estate in Prestigious Osterville | Private Beach, Pool & Hot Tub and Central ACbrbrbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrWaterfront Estate with Pool & Private Beach – 6 BD, Sleeps 15 – Ostervillebrbr*Waterfront location with private sandy beachbr*Amazing ocean views from every roombr* Pool & hot tub with pool house and full bathbr*Expansive deck and patio with panoramic viewsbr*Fire pit for evening gatheringsbr*Multiple king bedrooms br*Exclusive Osterville neighborhoodbrbrExperience the ultimate Cape Cod getaway at this stunning waterfront estate in the heart of Osterville. This classic Gambrel-style home is set on a private lot with six spacious bedrooms and six bathrooms (including one in the pool house), offering accommodations for up to 15 guests.brbrStep into the foyer and be welcomed by breathtaking ocean views. The expansive living room serves as the heart of the home, with plenty of comfortable seating and direct access to a large deck overlooking the water. The open-concept flow continues into the dining area and fully equipped kitchen, ideal for meals and entertaining. A convenient half bath and a first-floor bedroom with two twin beds complete the main level.brbrUpstairs, generously sized bedrooms with stunning water views provide space for everyone.brbrBedroom 2: King bed + twin with trundlebrBedroom 3: King bed, with full bath across the hall (walk-in shower)brBedroom 4: Twin bed, shares bath with Bedroom 3brBedroom 5: King bed with private bath (shower/tub)brBedroom 6: King bed + twin with trundle, private bath with showerbrbrThe outdoor spaces are where this estate truly shines. Relax on the expansive patio or dine al fresco on the deck while soaking in panoramic water views. Private steps lead down to your own sandy beach for swimming and sunbathing. After a day of exploring, unwind in the heated pool or hot tub, or rinse off in the pool house with its own full bath. As evening falls, gather around the fire pit for marshmallows and conversation under the starbrbr-Osterville Village (shops, restaurants, farmers market): 1 mi (4 min drive / 20 min walk / 8 min bike)br-Dowses Beach: 2 mi (6 min drive / 30 min walk / 10 min bike)br-Craigville Beach: 5 mi (12 min drive / 1 hr 20 min walk / 25 min bike)br-Main Street Hyannis: 7 mi (15 min drive / 1 hr 50 min walk / 35 min bike)br-Hyannis Harbor (ferries to Nantucket & Martha’s Vineyard): 7.5 mi (16 min drive / 2 hr walk / 35 min bike)brbrThis exceptional property combines luxury, comfort, and classic Cape Cod charm—perfect for family vacations or group retreats. Once you stay, you’ll want to return summer after summer.brbr***THIS PROPERTY CAN NOT BE USED FOR EVENTS***brbr***THE POOL AND HOT TUB CLOSE AT THE BEGINNING OF SEPTEMBER AND OPENS IN JUNE***brbr***PLEASE NOTE: THERE IS CONSTRUCTION GOING ON AT THE HOUSE NEXT DOOR, AT TIMES IT COULD BE VERY LOUD. WORK IS BEING DONE BOTH INSIDE AND OUTSIDE THE HOUSE.***brbr***LIMITED CELL PHONE SERVICE, BUT CAN CONNECT TO THE WIFI.***brbrbrKINLIN GROVER COMPASS VACATION RENTALSbrbr****CENTRAL AIR CONDITIONING****br****FREE WIFI****br****LINENS AND TOWELS INCLUDED - SHEETS AND TOWELS - BEDS MADE ****br****PETS CONSIDERED AT OWNER'S APPROVAL- DOGS ONLY - PET FEE $ 250.00 -REFUNDABLE PET SECURITY DEPOSIT OF $500.00 ****br****NO SMOKING****br****SATURDAY TO SATURDAY RENTAL****br****NON REFUNDABLE $220.00 RESERVATION FEE;$30.00 DAMAGE PROTECTION FEE;GUEST SERVICE FEE ;ALL APPLICABLE TAXESbr****$1500.00 REFUNDABLE SECURITY DEPOSIT****br**** NIGHTLY RENTALS IN OFF SEASON STARTING 8/30, 3 NIGHT MINIMUM, CLEANING FEE OF $600.00 ON NIGHTLY RENTALS***brbr**** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrKGC-TMADO

6

Bed

5

Bath

15

Sleeps

$1125.19

/ Nightly

Private Vacation Home

Large home in the heart of Osterville Village, sleeps 11

Osterville, Massachusetts, United States

LARGE-6BD Home--A/C, Amazing Location- Walk to Osterville Village and Dowses Beach-Great Private Backyardbrbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbr- Walk to Osterville Villagebr- Great location, near Restaurants and Shopsbr- Large Private Backyard with Deck, Patio Furniture, Grill and Outside Showerbr- Short stroll to Dowses Beachbr-Central A/Cbr-Landlord Beach PassbrbrStep inside this spotless and spacious 6-bedroom, 4-bath Osterville home and feel right at ease. The entryway welcomes you into a formal dining room, perfect for family meals and celebrations. Just beyond, the well-equipped kitchen with its casual dining area is ready for quick breakfasts before a day at the beach.brbrThe comfortable living room is the heart of the home, offering a cozy spot to unwind. On this level, you’ll also find two full baths, a laundry area, and two bedrooms — one with a Queen bed and another with two Twins.brbrHead upstairs and discover the spacious primary suite: a Queen bedroom with a private bath and Jacuzzi tub. The second floor also offers three additional bedrooms — one with a Queen bed, and two with Full beds — plus another full bath.brbrOutside, enjoy a private backyard with a deck for outdoor dining, a grill and a large enclosed outside shower.brYou will love the location of this large home and the Village of Osterville is so much fun, with it's Farmers Market, unique shops and great restaurants!brbrTV- Xfinity CablebrWasher and Dryer in Laundry Room off the Kitchenbrbrbr-Dowses Beach – ~1 milebr-Osterville Village (shops, restaurants, ice cream) – ~0.7 milesbr-Craigville Beach – ~4 milesbr-Hyannis (harbor, ferries, nightlife, shopping) – ~6 milesbr-Mashpee Commons (shopping & dining) – ~7 milesbr-Cape Cod Mall – ~7 milesbr-Golf Courses (several nearby) – within 5–10 milesbrbrKINLIN GROVER COMPASS VACATION RENTALSbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* NO PETSbr* OCCUPANCY: 11br* PARKING FOR 4 VEHICLESbr* CENTRAL AIR br* SHEETS AND TOWELS INCLUDED, BEDS MADEbr*LANDLORD BEACH PASSbr*220 NON REFUNDABLE RESERVATION FEE;30 damage protection fee;guest service fee and all applicable taxesbr*400 CLEANING FEEbrbr****FREE ACTIVITIES INCLUDED****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrClick the Xplorie button or visit the Free Activities page to see the free fun included with this Kinlin Grover Compass rental! Activities and availability are subject to change.brbrAs a guest of Kinlin Grover Compass, you'll receive free golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrbrKGC-TPATR

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$1183.29

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Private Vacation Home

Osterville Cape Cod-Style Home - One Block from North Bay!

Osterville, Massachusetts, United States

Osterville on Cape Cod. Pleasant Cape Cod-style home one block from North Bay just off Bay Street. Walk to village and shops. This house was renovated in 2009 and 2013. Solar panels were added in 2017. Ecotourism! Face Book page is Osterville vacation rentals. brbrPlease inquire for discounts in the September to May booking window.brbrThis Non-Smoking home features a large family room with dining area and a formal living room and dining area. Five bedrooms, four baths plus game room and bath on lower level. Four of the five baths have been expanded, renovated and completely updated. Two zone central air and heat. Attic fan. Screened in porches, flagstone terrace, fenced back yard, Master bedroom deck. Two bedrooms with French doors to another deck. Well equipped beautiful kitchen. Laundry room. Mature gardens.brbrOff season month long or more bookings are welcome at 4000.00 a month plus utilities. A discount will be applied to the lease rate. brbrKeywords: Osterville Cape Cod Family Home Bay Street Off season leases

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$477.26

/ Nightly

Cottage

Charming cottage near Osterville Village and Dowses beach RPMS094

Osterville, Massachusetts, United States

Michelle Sylvia rental collection home. This is the most charming and updated cottage in the village that you will find! Just 1 block to all Osterville shops and restaurants. This stunning two bedroom gem is totally turnkey with custom and designer details throughout. The pictures say it all! Central air, gas fireplace, hardwood floors, vaulted ceilings, granite countertops, stainless steel appliances, and dining deck in rear. The perfect village location. Short bike ride to Dowses Beach. Pets are not allowed.brbrHOME amenities: beach pass, beach towels, beach chairs, charcoal grill, coffee maker, all linens included starter supply of items for stay.brbrAll applicable taxes and fees apply.

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Select Dates for Price

Private Vacation Home

In the Heart of Osterville Village, Newly renovated, Pets considered RPMS087

Osterville, Massachusetts, United States

Michelle Sylvia rental collection. LOCATION!! In the Heart of Osterville Village. Walk to town, shopping, dining, beaches, golf, boating... brbrWonderful front porch affords you privacy, yet allows you to relax, unwind and watch the world go by. The home has been renovated from top to bottom, everything is brand new. Curl up on the sectional and watch a movie together or hang out on the porch for morning coffee. Gourmet kitchen, dining area, half bath, laundry and primary suite with king bed all on first level. Make your way to the second level with a second primary suite with full bath as well as two more bedrooms. One with a queen with relaxing deck and the other with a bunk set. Full bath in hall. brbrBack yard has patio with seating and gas grill as well as a fire pit. Pets considered with owner approval and an added pet fee. Beach pass provided. brHOME amenities: fire pit, gas grill beach pass, beach towels, beach chairs, K cup coffee maker, all linens included starter supply of items for stay. brbrAll applicable taxes and fees apply.

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$792.98

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Private Vacation Home

Osterville 4BD on Wianno 2nd Fairway! Walk to village/marina or bike to beach.

Osterville, Massachusetts, United States

Traditional Osterville Cape Cod home located on the second fairway of Wianno Country Club for nice breezes and quiet. Enjoy all the town of Osterville has to offer with a short walk to the village, town tennis/pickle courts, Crosby marina, and a quick bike ride or drive to Dowses Beach (1.5 miles). Beach pass provided.brbrSpacious first floor with living room, sun room, dining room, kitchen and bathroom. Four upstairs bedrooms, 3 with twin beds plus master with a king, and second full bath. Additional office space with multiple screens for when you need to get in a couple hours of work while away.brbrUpdated kitchen with new cabinetry, flooring, and counters. Central A/C for 4 bedrooms upstairs. Outdoor firepit. Plenty of parking at rear of house. Separate garage with ping pong, beach chairs and toys/games for your use. One week minimum stay..brbrKeywords: Osterville, MA, Dowses Beach, Osterville Village, Crosby Boat Yard, Cape Cod, Barnstable, Osterville, golf, Wianno, vacation, Craigville Beach

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$4678.85

/ Nightly

Private Vacation Home

Osterville pool rental near beach. Back yard paradise!! RPMS138

Osterville, Massachusetts, United States

Michelle Sylvia luxury collection. Exquisite 6-bedroom luxury pool home nestled on Sea View Avenue in Osterville, Cape Cod, offering an unparalleled blend of sophistication and coastal charm. This stunning summer rental is located in close proximity to Dowses Beach and the picturesque Osterville village, providing an idyllic retreat for the perfect Cape Cod getaway.brKey Features:brSIx bedrooms: This spacious residence boasts five elegantly appointed bedrooms, providing ample space for relaxation and comfort.brBonus Sleeping Area: In addition to the bedrooms, enjoy a bonus sleeping area that adds flexibility for accommodating additional guests. This is located on the 3rd floor with a full bath, TV room and double bed.brbrPrivate Pool: Immerse yourself in luxury with a private pool, perfect for refreshing swims and leisurely lounging under the warm Cape Cod sun. Enjoy the built in outdoor kitchen, hot tub and fire pit for all your vacation fun. brSea View Avenue Location: Situated on the prestigious Sea View Avenue, close to all Osterville offers. brProximity to Dowses Beach: Enjoy easy access to Dowses Beach, where sun, sand, and surf await. Create lasting memories with family and friends in this coastal haven. Beach pass provided.brClose to Osterville Village: Explore the charm of Osterville Village, known for its quaint shops, fine dining establishments, and a vibrant local atmosphere.brbrThis luxury pool home on Sea View Avenue is a haven of tranquility, offering the perfect blend of upscale living and coastal beauty. Ideal for those seeking a memorable and indulgent Cape Cod summer rental experience.brHOME amenities: fire pit, hot tub, outdoor shower, beach pass, beach towels, beach chairs, gas grill, K cup machine, drip coffee maker, all linens included starter supply of items for stay. brbrEach Robert Paul Vacation Rental reservation includes a dedicated guest services and protection program, designed to ensure a seamless and worry-free stay. This program encompasses reservation administration and damage protection for incidental, self-reported occurrences. Following your booking inquiry, a member of our local Cape Cod team will personally connect with you to confirm the details of your stay and review any additional protections specific to the home. All applicable taxes and fees are applied in accordance with local and platform requirements.brbrSecond level King with full bath/ shower, king with full bath/shower, queen, king, king plus 2 full baths both with tub shower combo,brThird level, TV room, full bath and double bed

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12

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$2157.87

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Private Vacation Home

BRAND NEW LISTING-Amazing Waterfront 5BD Private Setting-Pool & Hot Tub-Sleeps 10-Osterville-Beach Permit Included

Osterville, Massachusetts, United States

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$555.79

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Private Vacation Home

Charming home with open layout, deck, grill, AC, W/D, & yard

Osterville, Massachusetts, United States

Wisteria HavenbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your perfect Cape Cod getaway in Osterville! This delightful 3-bedroom, 3-bath home is nestled in a serene neighborhood that backs up to a picturesque Wildlife Sanctuary, offering a tranquil retreat for families and friends alike. As you step inside, you'll be greeted by an inviting open floor plan adorned with cathedral ceilings and beautiful hardwood flooring, creating a warm and welcoming atmosphere.brbrThe fully stocked kitchen is a chef's dream, featuring a breakfast nook, breakfast bar, and a spacious dining room table, making it effortless to enjoy meals together. Step outside to the large open deck, where you can unwind on the wrought iron patio set, fire up the gas grill, and dine under the enchanting wisteria-covered pergola—perfect for evening barbecues and gatherings.brbrThe home offers ample sleeping arrangements, with a spacious primary bedroom featuring a king bed and private bath, along with two additional queen bedrooms—one with its own private balcony. The finished walkout basement provides extra space for relaxation, complete with a sitting area and laundry facilities, ensuring you have everything you need for a comfortable stay.brbrLocated just 2.5 miles from Dowes Beach and minutes from Osterville Village, you'll have easy access to shopping, dining, and a variety of outdoor activities. Whether you're beachcombing, kayaking, or simply enjoying the beauty of the surrounding nature, this charming home is the ideal base for your Cape Cod adventures. Book your stay today and experience all that Osterville has to offer!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

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$716.4

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Private Vacation Home

Cape escape with patio, grill, firepit, outdoor dining, W/D

Osterville, Massachusetts, United States

Osterville OdysseybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrMake your home away from home at this central Cape Cod retreat. Ideally situated between Hyannis and Mashpee, this home boasts convenient access to Joshua's Pond, only a mile away. Explore a great selection of local shops and dining in downtown Osterville, a mile away. This beautiful property is close to Burgess Park, which offers a playground, basketball courts, and a small pond. Dowse's Beach and Craigsville Beach are also less than three miles away, making this the perfect spot for a summer vacation.brbrThe peaceful and private backyard comes complete with a spacious patio furnished for outdoor living with a gas grill, covered dining table, and firepit lounge area, which includes a fire table.brbrLower and main floor living areas each feature comfortable seating and smart TVs for flexible entertainment options. The main floor is bright and airy, with an open layout connecting the kitchen to promote group gatherings. A full suite of stainless steel appliances, including a dishwasher, and expansive counter space, come ready and equipped for home cooking. There's seating at the breakfast bar and the dining table for family meals. Modern essentials include baseboard heating, mini-split air-conditioners, free WiFi, and a private washer/dryer.brbrTHINGS TO KNOWbrbrParking notes: There is free parking available for 4 vehicles.brbrSecurity camera details: 1 Front Entrancebr2 Back EntrancebrbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

3

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3

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6

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Vacation Rentals By Owner In Osterville, MA

$790.38

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$1183.29

$477.26

$792.98

$4678.85

$2157.87

$555.79

$716.4

Rent a place that suits your needs

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