Vacation Rentals By Owner In Osterville, MA

A spacious and welcoming home in a wonderful location. This home allows plenty of room for multi families to vacation together. The large fenced in yard with built in gas fire pit, and inground pool with sunken hot tub also allows for all to gather and enjoy the Cape Cod sunshine , With a chef's kitchen and open living area all can cook, enjoy a cocktail and gather. The home is in a great proximity to beaches, boating and more. Mid Cape location allows access to prime Cape Cod attractions, beaches and Marinas.

Expansive Cape Cod Family Retreat

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$389.9

BBQ Ready | Recently Renovated | Convenient Main St LocationbrbrStep into Cape Cod living at this 2-bed, 1-bath Osterville vacation rental — where Massachusetts village vibes and coastal adventures merge in one inviting getaway. You'll enjoy a prime location on Main Street, beaches within 2 miles of the cottage, and a private patio for quiet evenings at home. Whether it’s sun and sand or lobster rolls and oysters, you'll find what you’re looking for here at this quintessential New England abode!brbr-- THE PROPERTY --brbrC0550080200 | 16633304brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 1 queen bedbr- Living Room: 1 full sleeper sofabrbrINDOOR LIVINGbr- Smart TVbr- Dining table, breakfast barbrbrOUTDOOR LIVINGbr- Private patio, outdoor dining areabr- Gas grillbrbrKITCHENbr- Refrigerator, stove/ovenbr- Keurig coffee maker (starter coffee provided)br- Toaster, microwavebr- Cooking basics, dishware & flatwarebrbrGENERALbr- Free WiFi, keyless entrybr- Central A/C, electric fireplace, ceiling fansbr- Linens & towels, trash bags & paper towelsbrbrACCESSIBILITYbr- Exterior steps required for entrybr- Single-story homebrbrPARKINGbr- Driveway (1 vehicle)br- Free street parkingbrbrADDT’L ACCOMMODATIONS br- 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 and renowned Cape destinations year-roundbr- 0.6 miles to Armstrong-Kelley Parkbr- 3 miles to Craigville Beachbr- 7 miles to Hyannis Harborbr- 7 miles to Cape Cod Gateway 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-inbrbr Additional INFORMATIONbr- This single-story home requires exterior steps to accessbr- This property is heated via electric fireplace. Central air conditioning is provided

Cottage

Walk to Shops & Dining: Cozy Osterville Cottage

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$329.88

Our quaint cottage is located just a minute's walk from Osterville's village center, with its upscale shopping, dining and charming ambiance. It's a quick bike ride or short one-mile drive to the beach and just a ten-minute drive to Hyannis proper or any one of a number of Cape Cod villages. Although our place will accommodate up to 3, it is best as a romantic getaway for a couple, an excellent place for a friends' weekend jaunt, or a comfy spot for a solo adventurer. Our place is not appropriate for children. We do include towels and linens for our guests as well as a beach pass.brWe prefer check-in no later than 7 pm

Cottage

Charming Cottage Getaway

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$1932.78

A five minute walk to Osterville's Wianno Club on Seaview Ave and to Dowse's Beach, this four bedroom, four bath home was completely renovated in winter 2019. All new kitchen, 2 new high-end bathrooms and french doors out to a new, covered back porch. Heavy-duty teak table and chairs on covered porch can easily accommodate twelve with extra chairs pulled up to table. brbrThe sunny and open kitchen has high ceilings, stainless steel appliances, a Thermador refrigerator, Thermador six burner gas range, Thermador dishwasher, custom maple cabinets, white Corian counter tops and a center island topped with quartzite. New open concept floor plan is what was formerly a galley kitchen, living room and separate eating area. This combined space (Great room) also looks out onto the beautifully planted front yard, a front covered porch with rockers, and the lush and private back yard and pool, heated at your option. Pool area is fenced for safety, has two round tables with chairs that seat 9, five chaise lounges, two outdoor heated showers and a storage box for pool toys. brThe entire house is WHEEL CHAIR ACCESSIBLE (but not ADA compliant) since it is basically all on one level. The step down family room is two steps down from the rest of the house but is open to the other rooms and anyone with mobility issues can still take part in things fairly easily.brbrThere is driveway parking for 5 normal sized cars and we have an assortment of five bicycles, two kayaks with life jackets & paddles, a John Deere pull wagon, a ride-on toy for little ones, various pool/beach toys, beach blankets, and beach chairs.brbrFor rainy days there is a new Game room on the lower level with state-of-the-art air hockey table from Frontgate (with automatic score keeping and crowd cheering!) and a foosball table. Cards, games, DVDs etc are provided. Three flat screen TVs with Xfinity package provided. New Cape Cod Cornhole game is provided as well. brbr#### New laundry room on the lower level with two new (2018) Electrolux full size machines, iron, ironing board and hanging rack for handwashables. Laundry detergent, starch etc is provided.#####brbrbrSince owners are enthusiastic cooks and love to entertain, the kitchen is fully equipped with pots and pans, XL lobster pot and utensils, dishes, bowls, flatware, glasses etc. All linens are included. No need to bring extras unless you have very specialized needs. We provide a beautiful new, full size crib, two baby gates, and a new high chair. Any other specialized equipment you need we ask you to please bring with you.brbr****All rooms are kept very comfortable with central air conditioning, provided by a Fujitsu mini-split ductless air conditioning system. It is new, virtually silent, and very efficient, bringing the temperature to a comfortable level in minutes. Owners' family business specializes in the installation and maintenance of these systems so the units are kept in great working order.brbrbr**** ALL CHECK-OUT PROCEDURES MUST BE FOLLOWED AS STATED, OTHERWISE WE MAY HAVE TO DEDUCT EXTRA CLEANING/ ORGANIZING FEES FROM THE SECURITY DEPOSIT ****

Heated Private Pool, Walk to beach & shops, fully renovated house

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$572.25

Osterville ~Total renovation recently completed and now available for the 2025-2026 rental season. Minimum age to rent is 28.brbrSet on a gorgeous tree-lined street in Osterville this 3 bedroom, 2,900 square foot, fully air-conditioned home has been updated to perfection. There are new hardwood floors on the first two levels of the house and new flooring on the lower level.brbrThe main floor consists of a stunning new kitchen with white shaker cabinets, stone countertops and stainless steel appliances. It has a large living room that spans from the front to the back of the house. The open dining area leads to the sunroom through sliding doors. The four season sunroom with a/c and ceiling fan overlook the private yard. The deck off of the sunroom is the perfect place to unwind after a day at the beach! The main floor also has a new half-bath off of the foyer.brbrThe second floor has two spacious bedrooms that are furnished with king-sized beds, twin beds are in the third bedroom, and a full-sized futon is in the bonus room. There is a new full sized bathroom on this level. Linens for the beds are included. Bath towel, face towel and washcloth is provided for each guest. brbrThe home has a finished lower level with a brand new full bathroom, pullout queen sofa bed, tv viewing area, full sized washer/dryer and ping pong table. The sliding glass doors lead to a seating area and gas grill.brbrNearby Joshua Pond is a five minute walk, and has a delightful freshwater swimming area with a beach, restrooms and a walking path. Our idyllic location is one mile to Dowses Beach, two miles to Craigville Beach and we provide a town beach pass to use at all Barnstable beaches. Beach towels and chairs are provided. It is a short walk to the shops and restaurants in Osterville Village and also to the walking paths in nearby Armstrong Kelly Park.brbrRenovations were complete in May of 2022. Make great Cape Cod summer memories in this beautiful home!

Osterville~Newly Renovated with central AC and beach pass

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$619.94

Enjoy modern Cape Cod living in this private 3-bedroom, 2-bath ranch-style home in Osterville. The home sleeps up to 8 and includes a Dowses Beach parking pass, offering free access to over 15 Barnstable-area beaches and ponds. Dowses Beach and Joshua’s Pond are both under a mile away, with Craigville Beach just a short drive.brbrPrivately set on a quiet residential street, the home is walkable to Osterville Village (0.5 mi) with shops, dining, and the beloved Fancy’s Market nearby. Inside, enjoy over 1,500 sq ft of living space with two separate living areas, Smart TVs, high-speed Wi-Fi, central A/C, and a fully equipped kitchen.brbrOutside, relax in a lush, private backyard with a furnished deck, grill, and classic outdoor shower—perfect after a day at the beach. Easy access to Hyannis ferries for day trips to Nantucket or Martha’s Vineyard, plus parking for up to four cars and private digital key entry.

Beach pass included • Modern 3BR Osterville retreat, walkable to village center

Osterville, Massachusetts, United States

Bed

2

Bath

8

Sleeps

Select Dates for Price

Discover the charm of Osterville from this inviting coastal residence, a thoughtfully designed two bedroom home with an additional upstairs sleeping space that offers comfort, style, and a classic Cape Cod atmosphere. Set minutes from idyllic Osterville village, this property is available for monthly rentals only, ideal for those seeking a longer, more immersive stay in one of the Cape’s most desirable areas.brbrInside, the home feels warm and welcoming, with sunlit rooms and an easy flow that encourages relaxation. The living area features comfortable seating and anchors the main level, while the adjacent dining space and well-equipped kitchen make it simple to prepare and enjoy meals at home. A full length front sun porch has multiple seatings areas. Soft colors and coastal accents create a soothing backdrop that complements the natural surroundings.brbrThe main level includes two serene bedrooms. The primary suite features a queen bed, TV, and an ensuite full bathroom with a separate shower and soaking tub. The guest room features twin bunk beds and has its own full bathroom with a shower next door. Upstairs, a spacious bonus area provides additional sleeping accommodations with a queen bed in a cozy hideaway that feels tucked beneath the eaves.brbrOutdoors, the setting reflects everything people love about Osterville. Mature landscaping, peaceful surroundings, and outdoor seating areas invite you to unwind and enjoy gentle breezes and quiet evenings. The property includes a guest house next door where the caretaker resides, offering on-site support while maintaining the privacy of your living space.brbrFrom this location, you can experience the best of village life. Beaches, boutique shops, cafes, restaurants, and scenic walking routes are within easy reach, making it simple to settle into a memorable Cape Cod rhythm. Whether you spend your days discovering local shops, exploring the 45 acres of conservation land behind the home, or enjoying the village’s coastal charm, you’ll return each evening to a comfortable residence designed for rest and ease. The provided Barnstable beach pass will make enjoying the multiple local beaches a breeze.brbrMonthly minimum rentals only during the season. All linens and towels are included with your stay. Pets are considered on a case by case basis. Central AC and heating throughout the home. Total cost subject to all applicable taxes and fees. All Robert Paul Vacation Rental bookings include a non-refundable $150-$250 fee that includes an administrative fee and damage waiver assurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional damage protection which may be required at this property.brbrPricing: June $16,000, July $20,000, August $20,000, September $16,000

Relaxing Cape Cod Stay in a Charming Osterville Setting RPAM121

Osterville, Massachusetts, United States

Bed

2

Bath

6

Sleeps

$609.58

3 Bedroom - 1.5 Baths - Sleeps 6brDuring peak summer weeks, it is typical for our properties to require a 7-night stay, Saturday-Saturday, but if you have unique dates please reach out to our Reservation Specialist. Most of our homes offer a 3-night stay minimum in the off-season.brComplimentary Linens Service Provided: This includes bedsheets, bath, beach, and dish towels for every bed, home and total home occupancy.brWe offer a 4 pm Check-In and 10 am Check-OutbrbrInviting getaway with beach pass included for easy beach access. Enjoy a bright sunroom, open living spaces, a fire pit, and outdoor dining. Perfect for families and groups seeking a comfortable, well-equipped stay designed for relaxation and effortless seaside enjoyment.brbrOwners share why they love their home: brWelcome to Olde Millie. We grew up on the Cape, near the Cape, or have family on the Cape — Centerville, Osterville, Hingham, Sonoma (ok, not the Cape) — but all four of us are tied to Barnstable in some way, and Millie has been in our family for years. What we love most is the patio at sunset, the fire pit going, and Dowses Beach a ten-minute walk away. We hope she's all of that for you too.The house is walking distance to restaurants, coffee shops, a grocery store, liquor store, ice cream shop and loads of cute shopping. Olde Millie comes with a beach pass for your car to use at all Barnstable Beaches (we recommend walking to Dowses Beach to avoid waiting in line to get in as it has limited parking). When you stay at Millie, we hope you'll feel like you, too, are in you're hometownbrbrLet us tell you about this home:brWelcome to this charming 1910 Cape Cod cottage, where classic character meets thoughtful modern updates to create a warm, inviting, and effortlessly comfortable seaside getaway. Designed with families and groups in mind, the home offers a functional layout that blends cozy gathering spaces with easy coastal living.brbrAs you enter, you're welcomed into a bright sunroom with comfortable seating that creates an inviting first impression. It serves as the heart of the home, with easy access to both the living room and kitchen for a natural flow throughout the main living spaces.brbrThe sunroom opens directly into the living room, enhancing the home's open feel. The living room offers classic Cape Cod charm, with barn doors connecting back to the sunroom for a cozy yet airy space ideal for relaxing or spending time together. It also features a large TV and flows directly into the kitchen, continuing the connected layout.brbrThe fully equipped kitchen features stainless steel appliances and a central island with seating. The kitchen flows naturally into the dining area, which includes a table for shared meals, along with a convenient bar and computer workspace for remote work or additional dining flexibility.brbrCompleting the first floor is a conveniently located bedroom, along with a half bath just off the kitchen for added ease.brUpstairs, guests will find a full bathroom along with the remaining sleeping arrangements, offering a comfortable and private retreat after a day at the beach.brbrBedroom 1 - Queen - First floorbrHalf bath - First floorbrbrBedroom 2 - Queen - Second FloorbrBathroom 1 - Full with tub and shower combo - Second floorbrBedroom 3 - 4 Twins - Second FloorbrbrStep outside to enjoy a fully fenced yard designed for outdoor living. A brick patio with full seating, outdoor dining table, fire pit, and gas grill creates the perfect setting for evening gatherings and meals. An enclosed outdoor shower adds a classic Cape Cod touch, ideal for rinsing off after beach days. A beach pass is included, along with beach chairs and a wagon stored in the shed for easy beach outings.brbrAdditional features include a basement laundry (please note the stairs are a bit low in height). There is a stone driveway on both sides of the home, comfortably accommodating up to three cars.brbrBlending timeless Cape Cod charm with modern comfort and thoughtful amenities, this home is perfectly suited for guests seeking a relaxed, memorable coastal getaway filled with ease and connection.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 has Keyless Entry for your convenience.brNo Smoking of anything containing tobacco, any other substance, and e-cigarettes, inside or outside of the home.brNo Pets are allowed inside or outside the home! brMax parking of cars at property: 3 - No parking on lawn anytime. brbrAdditional Information to Assist You: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 American Express, 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 homebrPlease 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 approximatebrDowses Beach 0.9 MilesbrFancy's Market 0.2 MilesbrCRISP Pizza 0.3 Miles brLong Beach 1.0 MilesbrCraigville Beach 1.3 Miles brStop & Shop 3.7 Miles brCape Cod Mall 6.0 Miles

Cozy Getaway with Beach Pass & Sunroom

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$4671.13

Brand new construction on Sea View Ave in Osterville. This little oasis boasts a pool, hottub, and tennis court. The home is located 100 yards from the little public beach at the corner of Wianno Ave and Sea View Ave. It is also only a quarter mile from the main entrance to Dowses beach.

Sea View Ave Brand New Construction - Pool Hot tub Tennis Court

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$753.05

The perfect setting for enjoying summertime in Osterville. This comfortable three bedroom home is overflowing with charm, while boasting modern amenities that will enhance your stay. The main floor has a very functional flow between the spacious dining room, large living room with oversized sectional, and front porch for relaxing. Off of the kitchen is a mudroom and half bath, which lead out to the seemingly endless backyard that backs up to Armstrong Kelley Park. The outdoor shower is a favorite feature for rinsing off those long beach days. The impeccable outdoor space includes a brand new gunite pool (2024), cabana house with gas fireplace and television overlooking the large patio. The patio has its own fireplace, as well as a giant dining table and comfortable lounge chairs. If you can peel yourself away from this personal oasis, the home also comes with a beach pass for parking at any Barnstable beach, the closest being Dowses Beach of Osterville less than 1 mile away. This estate is located just a short walk to Osterville's village center, which has ample shopping and dining options.brbrAbout the area: Osterville is a picturesque Cape Cod village peacefully located on Nantucket Sound, on the south side of Barnstable. The quaint village center boasts dozens of shops, restaurants and small businesses, and is a lovely place to spend an afternoon stroll. Grab lunch at Wimpy's for classic seafood, Crisp Flatbread for tasty pizza and pasta, or The Chart Room for a cocktail with a view. Surrounding the downtown are charming residential neighborhoods with tree-lined streets and stunning, classic Cape architecture to observe. You can find a body of water almost anywhere you turn in Osterville. Dowses Beach is the beloved beach on East Bay Road, where families enjoy sunny days on the Nantucket Sound side, or a more tranquil scene on the East Bay side. Boating is a fan-favorite pastime in Osterville, and the village has the marinas and bays to support it. If you have never been to Osterville, you are sure to fall in love with its timeless charm.

Osterville Village - New Pool Large Yard + Outdoor Entertaining Area

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$455.91

Summary:brbrWisteria HavenbrbrbrbrThe Space: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. The 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. The 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. Located 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! bThings to Know/b Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All 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. No smoking is permitted anywhere on the premises.

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

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$613.05

Summary:brbrOsterville OdysseybrbrbrbrThe Space: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. The 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. Lower 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. bTHINGS TO KNOW/b

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

Osterville, Massachusetts, United States

Bed

Bath

6

Sleeps

$550.4

NEW LISTING – Osterville Retreat – Large Private Yard – Close to Village, Beach & Pondbrbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrSleeps 8 | Central A/C & Mini-Splits | Expansive Yard | Outdoor Showerbrbr*Spacious private backyard with deck, grill & enclosed outdoor showerbr*Open-concept living with cathedral ceilings & abundant natural lightbr*Lower-level bonus living space with TV, games, & booksbr*Primary suite with king bed & private balconybr*Close to Osterville Village-John's Pond and Dowses BeachbrbrStep inside and you’re welcomed by soaring cathedral ceilings and sun-filled windows in the open-concept living area. Relax on the plush sofa with a movie on the large TV, or gather around the dining table after preparing meals in the fully equipped, updated kitchen. The spacious island is perfect for morning coffee and planning the day’s adventures.brbrOn the first floor, a comfortable queen bedroom sits just steps from a full bath with a tub/shower. Downstairs, the lower-level living area provides extra space with a TV, video games, board games, and books—perfect for kids or family hangouts.brbrUpstairs, the second floor features a charming bunk room with a twin trundle, along with the primary suite boasting a king bed and private balcony overlooking the yard. A shared hallway bath with a tub/shower completes this level.brbrThe expansive backyard feels like a private oasis, with plenty of room to relax and entertain. Enjoy afternoons on the deck, cook on the gas grill, or gather for al fresco dining. After a beach day, rinse off in the enclosed outdoor shower, then wind down around the firepit while roasting marshmallows under the stars.brbrTV's for streaming your favorite showsbrCentral A/C upstairs & new ductless mini-splits on first floorbrWasher & dryer brbr-Osterville Village – 1 mile (3-min drive, 15-min walk, 6-min bike)br-Joshua’s Pond – 1 mile (3-min drive, 14-min walk, 5-min bike)br-Dowses Beach – 2.5 miles (6-min drive, 10-min bike)br-Craigville Beach – 5 miles (12-min drive)br-Mashpee Commons – 7.5 miles (15-min drive)br-Downtown Hyannis/Harbor & Ferries – 7 miles (15-min drive)brbrNightly off-season rentals available (3-night minimum)br$175 cleaning fee applies to nightly rentalsbr*$220 non-refundable reservation fee; $30 damage protection fee; guest services fee; all applicable taxesbrKINLIN GROVER COMPASS VACATION RENTALSbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO SMOKINGbr* NO PETSbr* OCCUPANCY: 8br* PARKING FOR 3 VEHICLESbr* DUCTLESS MINI SPLIT AC DOWNSTAIRS, CENTRAL AIR UPSTAIRSbr* SHEETS AND TOWELS INCLUDED,BEDS MADEbr*BEACH CHAIRS INCLUDEDbrbr****FREE ACTIVITIES INCLUDED**** Kinlin Grover Compass Vacation RentalsbrTo 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 golf tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities!brbr**** CANCELLATION/REFUND POLICY ****brbrUpon 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-TSMIT

Osterville, Private Yard, Close to Osterville Village, Sleeps 8

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$585.99

Relax in this sunny Osterville home near village cafés and 3 beaches. The open main floor has a roomy living area and eat-in kitchen w/ two comfy bedrooms and a full bath. A finished lower level w/ private suite with bath, lounge, and laundry. Step outside to a yard with a dining table +patio, grill, outdoor shower, firepit with chairs. 4 adult bikes will take you straight to town & 15 mins Craigsville beach bike ride; Hyannis and major routes are close by. Fast Wi-Fi, beach gear, and BEACH parking pass included.brbrMain floor:br- Open living room with Roku TV, and dining table.br- Bedroom 1. King bed, dresser Sleeps two. Has TV.br- Bedroom 2. Two single beds and a Roku TV. Sleeps two.br• Full bath with tub/shower combo and hairdryer.br• Fully equipped eat-in kitchen with deck access.brbrLower levelbr• Bedroom 3. Full bed, closet, and en-suite bath with step-in shower. Sleeps two.br• Game lounge with Google TV, ping-pong table, board games, and laundry area. Pull-out queen sofa that sleeps two.brbrOutdoorsbrShaded yard with deck, grill, firepit, lawn games, and an outdoor shower. Six-car driveway. brbr4 adult bikes + helmetsbrbrRing doorbell is the only camera on site.

Cape Cod getaway near Craigville Beach

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$1353.78

Three bedroom carriage house on private oceanfront estate in the Wianno section of Osterville. Originally built as stableman's quarters, this house has been renovated into an adorable cottage-like home. Screened in porch leads to a large living area with hardwood floors, cathedral ceiling, ceiling fan, HVAC, and bright sunlight throughout. Kitchen, with eating area, has original cabinetry with modern appliances. Bath with shower. washer/ dryer. Upstairs has three bedrooms and one bath with walk in shower. Room sizes vary but each room is light and airy. The property is on approximately three acres of oceanfront property overlooking East Bay, Dowses Beach and Nantucket Sound. The private beach is at the end of the wooden walkway on the property Or you can walk to the beach at the end of Wianno Ave or walk to Dowses Beach. The saltwater bay has a small dock at the edge of the property which is great for crabbing or kayaking! The landscape is beautiful with lots of space to kick a soccer ball or grab a chair to sit and read!br brLocation is spectacular. Approximately one mile from the center of town. great for walking, running, cycling. Beautiful beaches with warm gulf stream water. Very charming and clean living space.br br br br brbrKeywords: House

Charming Carriage House on Private Oceanfront Estate

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$610.4

Gorgeous, spacious, and fully appointed home in OSTERVILLE VILLAGE! 4 bedroom, 2.5 bathroom home with large eat-in kitchen with seating for10. Open great room with cathedral ceilings and french doors to back patio. Three bedrooms on first floor, including main bedroom with king bed and attached half bathroom. Full bathroom on main level with tub/shower and laundry chute. Wide spiral staircase leads to second level with large open loft room with 2 comfortable futons and a huge bedroom with a queen bed, 3 twins, 2 closets and full bathroom in hall. The attached one car garage has access to the full sizable basement. Washer/dryer in basement. Beautiful grounds and large back patio, gorgeous hot tub and outdoor shower. brbrWhat adults will love:brThis is a beautiful, sparkling clean, home with central air conditioning in a quiet, upscale neighborhood that is a 3 minute drive to East Bay and Dowses Beach and an quick bike ride or 1 mile walk to town center where you will find Wimpy's, Fancies, Crisp, DD's and great shopping. The kitchen is fully equipped to make everything from burgers to a gourmet meal. The chef in the family will appreciate the gas stove, cooktop and large island. brbrThe private backyard with fire pit, grill, Lounge Chairs and Table with plenty of room to sit after a great day at the beach. There is also an outdoor shower to rinse after beach/lake. Relax and unwind in the hot tub after a long day sightseeing or at the beach!brbrTowels and bedding as well as beach chairs are included and there is a large washer and dryer so you can pack light.brbrCozy family room with Bose stereo, 65 flat screen TV and high speed Wi-Fi. brbrStroll to charming town with plenty of Boutique shopping and dining. brbrAbout a mile to Armstrong-Kelley Park, which is a garden and woodland oasis and treasured community resource, providing residents and visitors alike with a peaceful place to stroll. There are may famous restaurants in town and beautiful new tennis and pickleball courts. brbrCape Cod Ferries are located only 15 minutes away which will take you to Nantucket or Martha's Vineyard for a day trip. Also you will find the Pirate Ship for the kids, Sunset Cruises, fishing excursions or a boat tour of Hyannis Port/Kennedy Compound.brbrFor the travelers who like to Shop, plenty of shopping to do in Osterville Boutiques, Hyannis on Main Street, the Cape Cod Mall, or a quick drive to Mashpee Commons. Endless restaurants to choose from in our area also. We have a great list in our welcome binder.brbrFor the vacationers that love to golf, you have access to many beautiful breathtaking golf courses with in a few miles of our home. If boating is your favorite pastime, you can bring your own boat (fits easily in our driveway) and launch it from several public launch areas. If you prefer to rent a boat (or kayaks, paddle boards) there are several places to rent or take lessons.brbrThings kids will love:brFirst they will want to climb the spiral staircase to the loft/gameroom where they will find plenty of board games, puzzles, toys and booksbrbrHome is on a quiet street for play or riding bikes and the backyard is perfect for games and sports. Many lawn/beach games as well as foosball in basement.brbrGreat ice cream shops close by like The Salty Cow, Gone Chocolate and Four Seas!

An Osterville Gem!!Very close to town and beach!

Osterville, Massachusetts, United States

4

Bed

2

Bath

12

Sleeps

$1541.26

Waterfront- 7BD-Deep Water Dock-Close to Osterville Village-A/C, Elevator and Beach Passbrbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbr*Deep water dock – bring or rent a boatbr*Small sandy beach area at the water’s edgebr*Elevator for easy access between floorsbr*Sunroom with panoramic water viewsbr*Mini-split A/C in all bedrooms and living areasbr*Landlord beach pass includedbrbrStep back in time with this amazing 7-bedroom, 5.5-bath classic Cape Cod home. Located right on the water, this property features a private deep water dock, perfect for bringing your boat or renting one to cruise over to Martha’s Vineyard for the day. Guests can also enjoy a sandy beach area right at the water’s edge.brbrInside, you’ll find a spacious eat-in kitchen with a huge center island, plenty of counter space, and all the amenities of home. The kitchen table faces large windows with gorgeous water views. Off the kitchen, a formal dining room with a large table offers plenty of space for your entire group.brbrThe grand living room is the heart of the home—featuring comfy couches, multiple seating areas, and picture windows facing the water. Need to catch up on work A private office space is conveniently located off the living room.brbrA sunny enclosed porch provides the perfect place to sip morning coffee while watching yachts go by—or enjoy evening cocktails while taking in the sunset.brbrHead upstairs to the second floor, accessible by both a staircase and an elevator. Each bedroom has its own coastal charm:brbrSlipper Shell Room – 2 twin beds, Jack & Jill bath with showerbrScallop Room – Queen bedbrSea Star Room – 2 twins (convertible to a king), water viewsbrFull bath with showerbrSand Dollar Room – 2 twin bedsbrOyster Room (Primary) – Queen bed, en-suite with shower and soaking tub, corner room with water viewsbrThe third floor offers two more bedrooms:brNautilus Room – 2 twin beds, en-suite with shower and tubbrMoon Shell Room – King bed facing fireplace and water views, large closet, en-suite with shower and tubbrbrOutdoors, you’ll find a gas grill, enclosed outdoor shower, and a spacious lawn with incredible water views—perfect for family gatherings or special occasions. brbr-Osterville Village – 1 mile / 4-min drive, 20-min walk, 8-min bikebr-Dowses Beach – 2 miles / 6-min drive, 35-min walk, 12-min bikebr-Craigville Beach – 4.5 miles / 12-min drive, 25-min bikebr-Main Street Hyannis – 6 miles / 15-min drivebr-Hyannis Harbor & Ferries – 6.5 miles / 16-min drivebr-Mashpee Commons -8.0 miles / 19 -min drivebrbrFor larger events, there’s even a sister property available next door to rent together.brbrbr**USAGE OF THE DOCK WILL REQUIRE TENANT TO NAME BREEZY BLUFF ON TENANTS LIABILITY POLICY,AND APPROVAL FROM OWNER. REFUNDABLE SECURITY DEPOSIT IS REQUIRED AND APPROVAL FROM THE OWNER**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, 4 NIGHT MINIMUM IN OFF SEASON, WITH 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!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-TMILL2

Amazing updated waterfront home located in Osterville with a private dock, elevator and AC.

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$1478.69

Welcome to Wianno House! Renovated top-to-bottom in 2022, this home is the perfect for vacationers seeking luxury accommodations in the heart of idyllic Osterville. Stroll to the village, walk to Dowses beach or spend a lazy afternoon curled up with a book on the screened-in porch overlooking the spacious private yard.brbrFive Bedrooms, 4.5 bathrooms, Sleeps 10* - Two primary suites (#1 on the main floor, #2 on the second floor) each have a king bed and ensuite bathroom. Bedroom #3 has two full beds and is connected to Bedroom # 4 with two twin beds - they share a bathroom and are located on the second floor. Bedroom #5 has a queen bed on the main floor. For additional accommodations, there is a 4th full bathroom in the basement family room and an oversized outdoor shower off the patio.brbrWianno House is sunny and spacious with a seamless indoor/outdoor flow and any number of areas for family and friends to gather. The vaulted ceiling chef’s kitchen boasts a center island, professional grade appliances including 2 dishwashers, separate ice maker, large kitchen pantry, and countertop seating…everything for vacationers that love to cook together. The adjacent dining area seats 10.brbrTwo sets of French doors off the kitchen open onto the large screened in porch – ideal for lounging and cocktail hour. Beyond the porch is the large level backyard with mature plantings offering lots of privacy. The backyard features a large outdoor dining table, fire pit, gas grill and an oversized outdoor shower for rinsing sandy toes and showering under the stars.brbrThe generous living area on the main floor has a large HD television (connected to your favorite streaming services), comfortable seating and an antique game table for puzzles and game nights. The main floor also has a private office and powder room.brbrOne of the highlights of this wonderful home is the large, bright basement & recreation room. After a day at the beach, enjoy a round of pool or darts. Grab a cold drink from the wet bar and watch a movie with the whole gang on the large sectional. The basement includes a large laundry room with 2 washer/dryers, vintage sink and folding table.brbrWianno House is equipped with luxury hotel mattresses, fine European bedding, high quality bath and beach towels and spa bath products. Painted hardwood floors, beadboard ceilings, Kingsley Bates teak furniture, Waterworks fixtures, and zellige bath tiles round out the luxury coastal vibe.brbrThe rental comes with a beach pass for access and free parking at all public beaches inbrBarnstable, including Dowses Beach just ¼ mile away.brbr*Up to 12 guests will be considered with approval.brbrAbout the area: Osterville is a picturesque Cape Cod village peacefully located on Nantucket Sound, on the south side of Barnstable. The quaint village center boasts dozens of shops, restaurants and small businesses, and is a lovely place to spend an afternoon stroll. Grab lunch at Wimpy's for classic seafood, Crisp Flatbread for tasty pizza and pasta, or The Chart Room for a cocktail with a view. Surrounding the downtown are charming residential neighborhoods with tree-lined streets and stunning, classic Cape architecture to observe. You can find a body of water almost anywhere you turn in Osterville. Dowses Beach is the beloved beach on East Bay Road, where families enjoy sunny days on the Nantucket Sound side, or a more tranquil scene on the East Bay side. Boating is a fan-favorite pastime in Osterville, and the village has the marinas and bays to support it. If you have never been to Osterville, you are sure to fall in love with its timeless charm.

New Luxury Renovation in Prime Osterville Village: Five Bedrooms, Sleeps 10

Osterville, Massachusetts, United States

Bed

Bath

Sleeps

$1659.53