Vacation Rentals By Owner In Orleans, MA

$503.8

Walk to Nauset Historic Home

Orleans, Massachusetts, United States

Walk to Nauset Beach from this wonderful home. Once part of the historic Mayo Duck Farm and a 2/10 mile walk from beautiful Nauset Beach and the Atlantic Ocean. This home has been completely refreshed including some new furniture, new rugs and curtains, and even a new flat screen television! Steam up the lobster in the gorgeous fully equipped kitchen. Have your morning coffee on the back deck which offers peeks of the ocean. All bedrooms are located on the 2nd level which also has a 1/2 bath for convenience. The game table in the living/family room has games to challenge all age. If it is games you enjoy, a short drive will put you under the lights @ Eldridge Park in Orleans Center to watch the BEST baseball in the lower 48. Restaurants abound and the shopping, antiquing, craft fairs and theater are just the tip of the sand bar. Please note: the attached apartment is also available to rent for larger families or groups. Like so many of our repeat vacationers, visit our home and enjoy the memories for years to come.

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Sleeps

$654.94

/ Nightly

Private Vacation Home

Ocean Harbor Estates

Orleans, Massachusetts, United States

Beautiful 4 bedroom home located in Ocean Harbor Estates that offers tennis, footpath to saltwater association beach. A traditional Cape set up on a hill with a private back yard bordering a protected bird sanctuary. This home features 4 spacious bedrooms, kitchen with breakfast nook, comfortable living room, and large dining area with triple sliders to deck and private backyard. Kitchen is fully stocked and has gorgeous features including granite counters and tons of counter space. House is right across the street from the tennis courts so don't forget your racquets! East Orleans Village is 1.5 miles to the west-beautiful Nauset Beach is 1.5 miles to the east...ideal for gathering of active family members and friends! Electronics Description: One TV upstairs, One TV downstairs. New Outdoor Shower for 2023!

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Sleeps

$757.91

/ Nightly

Private Vacation Home

Close to Nauset Beach!

Orleans, Massachusetts, United States

Summary:brbr15562 - Surf Station: Close to Nauset Beach!brbrbrbrThe Space:brbrThe coastal breeze fills your lungs as you sip your morning coffee, starting your day off the best way the Cape can offer. With privacy, comfort, and decadent decor, come hang ten, at Surf Station. Stepping into this home, you’re greeted by the elegant open-concept living room and kitchen. A stone chimney centerpieces the space, with warm wood and soft colors giving the home a relaxing feel. Barnwood floors and exposed stonework give this home a unique rustic touch, while the modern attention to detail in the home makes you feel like you’re in the schiquest of vacation retreats. Sliding barn doors throughout the home are another fun addition to this home not often seen on the Cape. The primary bedroom, with queen bed and en suite full bathroom, completes the first floor. brUpstairs, natural light floods in from the large skylights, bringing the summer sun indoors. The open lofted area has a TV, seating area, and queen bed; you can even escape outside to the private upstairs deck. A private bathroom completes the lofted area with a unique copper sink with a natural patina. brbrOutside, a sprawling yard gives privacy and endless possibilities for vacation fun. The back deck is a great spot to grill up burgers or catch some sun. You can even explore Nauset Beach via your own private path down to the salty shores. If shopping is what you're after, head less than ten minutes up the road to Main Street in Orleans, full of shops and delicious food. brbrOther amenities include a washer and dryer, propane grill, and an outdoor shower. Whether you’re looking to dive into the waters of the Cape, or rest under the stars in the summer air, your home is ready for you at the Surf Station.brbrHome Details:br-Sleeps 4br-2 Floors (1st Floor + Lofted Area)br-2 Bedroomsbr-Bedroom #1: 1 Queen Bed w/ en suite Full Bathroom, 1st Floorbr-Bedroom #2: 1 Queen Bed, Lofted Areabr-2 Full Bathroomsbr-Bathroom #1: Full Bath w/ Shower, en suite, 1st Floorbr-Bathroom #2: Full Bath w/ Tub (No Shower), Lofted Areabr-Fully Equipped Kitchen w/ Dishwasherbr-Window A/C Unitsbr-Smart Lock/Self Check-Inbr-WiFibr-Smart TV/Streamingbr-Washer/Dryer (basement)br-Rooftop Deckbr-Ground Level Deck w/ Outdoor Dining & Loungingbr-Propane Grillbr-Outdoor Showerbr-Private Yardbr-NO Pets (fines remitted)br-3 Min Drive to Nauset Farms, Local Grocery Store, Dellibr-Less Than 10 Min Drive to Main St in Orleansbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0250852240brbrbrbrThe Neighborhood:brbrOceanside

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$566.77

/ Nightly

Private Vacation Home

Private Lake Access, Great for Families!

Orleans, Massachusetts, United States

Summary:brbr15577 - Lakeside Retreat: Private Lake Access, Great for Families!brbrbrbrThe Space:brbrAmidst the picturesque landscape of Orleans, Lakeside Retreat offers an idyllic escape with its prime location boasting private, direct access to the tranquil waters of Pilgrim Lake. Step into your own private sanctuary, where a private yard beckons you to immerse yourself in the serene embrace of nature.brbrInside, discover a space that effortlessly combines comfort and charm, providing ample room for multigenerational families to create lasting memories. Whether lounging indoors or venturing outside, every corner of Lakeside Retreat exudes warmth and invitation.brbrEmbark on aquatic adventures just steps away from your doorstep – stroll down to the water's edge or embark on a canoe excursion, soaking in the sun as you explore the nearby wonders. As evening descends, gather on the expansive back deck for a delightful barbecue, surrounded by ample seating that sets the stage for cherished moments with loved ones.brbrPet lovers rejoice, as Lakeside Retreat warmly welcomes your furry companions to join in on the vacation fun. Pilgrim Lake beckons, offering a serene backdrop for leisurely strolls or invigorating dips, while the convenience of nearby town beaches ensures endless opportunities for coastal exploration.brbrConveniently located less than 10 minutes from downtown Orleans, indulge in the culinary delights of acclaimed eateries such as Hole in One for a breakfast to remember, Viv's Kitchen for fresh salads and sandwiches, and Hot Chocolate Sparrow for a sweet finale to your day.brbrBefore diving in, be sure to consult the Orleans Town website for water quality swimming advisories for Pilgrim Lake, which may vary depending on the season.brbrEscape to Lakeside Retreat and experience a harmonious blend of comfort, convenience, and natural splendor – the perfect setting for your next unforgettable vacation.brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 7brBedroomsbr-Total 3br-1st Floor Bedroom: 1 King Bedbr-2nd Floor Bedroom: 1 King Bedbr-2nd Floor Bedroom: 1 Full Bed + 1 Twin BedbrBathroomsbr-Total 3.5br-1st Floor: Showerbr-2nd Floor: Showerbr-2nd Floor: Tub/Shower Combo -1st Floor: Half BathbrOther Amenities br-Window Units ACbr-WiFibr-Smart TVbr-Cable TVbr-Washer/Dryer br-Propane Grillbr-Water Sports: 1 Canoe w/Paddles/Life Vestbr-Indoor Fireplaces are not for guest use(fines remitted)br-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 3 cars maximumbr-C0470372240

3

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3

Bath

7

Sleeps

$580.84

/ Nightly

Private Vacation Home

Private Orleans Getaway Near Bakers Pond & Beaches (2422)

Orleans, Massachusetts, United States

Welcome to your perfect Cape escape! NEW TO RENTALS in 2026, this recently renovated Orleans home offers stunning hardwood floors throughout and is tucked away in a quiet, private neighborhood with deeded access to Bakers Pond, known for its crystal-clear water and peaceful sandy beaches.brbrIdeally situated, the property provides quick access to the highway for easy travel to neighboring Cape Cod towns and attractions. Downtown Orleans is just minutes away, offering eclectic shopping, scrumptious dining, world-class beaches, and endless activities including fishing, Cape Cod Baseball League games, scenic conservation trails, and more.brbrThe main floor is designed for togetherness featuring a sprawling family room that flows seamlessly into the dining area and centrally located galley kitchen. A bright and inviting sunroom adjoins this space, offering a pull-out sleeper sofa, TV, and a breakfast/card table all overlooking the private backyard. From here, step out to the spacious back deck, also accessible from the dining room, perfect for outdoor dining, relaxing, or grilling after a day at the beach.brbrThe expansive primary bedroom suite is conveniently located on this floor, offering a king bed, sliders to the deck, TV, and a private ensuite bath with a walk-in shower. A second bedroom with two twin beds and a full bathroom completes the main level. Upstairs you’ll find a large bedroom with a king bed and another comfortable bedroom with a queen, both sharing a full bathroom with a tub. The finished, carpeted basement offers extra space to spread out and includes a washer and dryer for added convenience during your stay.brbrWhether you’re seeking a peaceful retreat or a home base for Cape Cod adventures, this beautiful Orleans property offers comfort, convenience, and quintessential coastal charm. Your perfect vacation awaits! Dogs considered with an added fee. There is driveway parking for 4 cars. Short getaways available with an added cleaning fee. Save the cleaning fee by booking 7 or more consecutive nights. BOOK NOW! An administrative fee and applicable taxes may apply. brbrLinens not provided. Guests may rent linens or bring their own.

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$394.89

/ Nightly

Private Vacation Home

Charming, Renovated 1870s Home with Private Beach

Orleans, Massachusetts, United States

Relax on your own private beach on Pleasant Bay, only a ½ mile walk or drive through protected forest land. This charming, renovated historic (c. 1873) home in the exclusive Barley Neck area has a completely private yard and deck. 1-1/2 miles to East Orleans shops and delis, 2-1/2 miles to Nauset Beach.brbrSleeps six in three bedrooms: twin bunk bed, double bed, and king bed (or convert to 2 twins). Blankets, quilts, pillows, and mattress protectors provided; guests need to bring or rent sheets and towels. One full bathroom plus enclosed outdoor shower. Kitchen fully equipped — from microwave and dishwasher to herbs and spices. Clothes washer and dryer, phone, wifi internet, cable TV. Comfortably furnished. Books and puzzles for rainy days. No pets.

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$786.39

/ Nightly

Private Vacation Home

Walk to Nauset Beach, Updated and Cozy!

Orleans, Massachusetts, United States

Summary:brbr15581 - Beach Daze: Walk to Nauset Beach, Updated and Cozy!brbrbrbrThe Space:brbrDiscover your dream Cape Cod vacation in the heart of Orleans, just a short walk to Nauset Beach where you can spend your days frolicking in the waves or resting on the white sand beach. Let the sound of the waves gently crashing against the shore lull you into a state of total relaxation, or spend your mornings strolling to nearby Priscilla Beach to launch kayaks or canoes, with rentals available for delivery at Goose Hummock. Treat yourself to a cup of coffee at Whisk, or fresh sandwiches at Nauset Farms, just a 2-mile drive away. After a day of beach adventures, rinse off in the outdoor shower or gather around the propane grill for a laid-back barbecue. End your nights with a homemade ice cream from Smitty’s then, return to your private sanctuary, where a spacious backyard invites you to relax and enjoy the evening ocean breeze.brbrAfter a day enjoying all Orleans has to offer, return to your comfortable and sophisticated home where the warm wooden beams and updated interior provide the perfect setting to relax and spend time with your family. Central AC and all-new appliances ensure your stay is as seamless as it is stylish. This dog-friendly haven sleeps six across three cozy bedrooms: two on the ground floor (one queen and two twins) and a luxurious queen bedroom upstairs. With 2.5 bathrooms, including a full bath with a tub/shower combo on the ground floor, there’s plenty of room for everyone. brbrWhether you’re savoring quiet moments on the deck or exploring all Orleans has to offer, this home is your perfect coastal escape. Don’t wait—book your unforgettable Cape Cod getaway today!brbrHome Details:br-Dogs Welcomed (w/fee of $45/night per dog)br-Sleeps 6brBedroomsbr-Total 3br-Ground Floor: 1 Queen Bedbr-Ground Floor: 2 Twin Bedsbr-2nd Floor Bedroom: 1 Queen BedbrBathroomsbr-Total 2.5br-Ground Floor: Full bath, tub/shower combobr-1st Floor: Half bathbr-2nd Floor: Full bath, ShowerbrOther Amenities br-Central ACbr-WiFibr-Smart TVbr-Streaming Servicebr-Washer/Dryer br-Propane Grillbr-Outdoor Shower br-Please note outdoor amenities are available seasonallybr-Sheets and Bath Towels Provided with Beds made Upon Arrivalbr-Cleaned with Hospital Grade Disinfectantbr-Parking for 2 cars maximumbr-C0399902240

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$1441.81

/ Nightly

Private Vacation Home

Featured in Boston Globe- fully renovated cape w/ pool & modern barn pool house

Orleans, Massachusetts, United States

3/4 of a mile from Rock Harbor (sunsets and “flats” for swimming and beach walking) you will find a fully renovated / modernized 3000+ sf rambling antique cape on an acre of landscaped yard (with two more acres of woods behind). Also on property is a heated pool and a newly constructed custom modern 1,000+ sf barn / poolhouse. The landscaping is meticulous as are the furnishings, kitchen equipment, etc. The house has 4 bedrooms (king, queen, two twins, three twins) plus two additional built in standard twin beds in the upstairs hall. The primary (king) and queen bedrooms are on the first floor. The bedrooms with all the twins (plus the hallway built in beds) are on the second floor. In each bedroom you will find quality mattresses, high end bed linens, chests of drawers and empty closets. Bath and beach/pool towels are included. In the house there are three full baths, two on the first floor (one ensuite to the master, one directly across from the queen room) and one on the second floor (which has a shower/bathtub and double trough sink), plus two outdoor showers (one concealed and off a side deck attached to the house and one by the pool). There are two large living spaces, one at either end of the house, a dining room, breakfast table, bar area, office, large deck with ample dining and lounge seating, a second deck with grill off the kitchen, A/C, washer / dryer, wine fridge. Additionally, the pool house has a dining table, lounge furniture, a large patio also with designer furnishings, 1/2 bath, partial kitchen including fridge drawers and ice maker, second washer and dryer, loft with 3 hanging chairs beanbags and a game/dining table. The well landscaped yard contains a play set and large, flat backyard ideal for family games of whiffle ball or late night glow in the dark hide and seek. The house boasts only one TV, as we think there are better things to do on the cape! You'll have access to a YouTube TV account and can access your favorite streaming apps. The property is available (and has been used) for product shoots. The property is NOT available for parties / events. It's a very special spot ;)

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$675.26

/ Nightly

Private Vacation Home

Centrally located Orleans home w/ outdoor seatiing

Orleans, Massachusetts, United States

This charming 3 bedroom, 1 bathroom home has all you need for a perfect stay. The home is all on one floor, allowing for a socially pleasing experience with family or friends. Bedroom 1 features a queen bed and ample storage space for personal items. Bedroom two and three have 2 twins and a double bed respectively. The bathroom features a glass enclosed shower. The kitchen is fully stocked and equipped with all the tools necessary to create the perfect home made meal. With a large deck and ample yard space, this rental has all you need for your family getaway.

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$315.98

/ Nightly

Cottage

Antique Cottage with King Bed, Kitchen, Bath, Private Yard & Path to Arey's Pond

Orleans, Massachusetts, United States

Welcome to Captain Seth Sparrow Cottage. Finally relax at this unique and tranquil getaway. One bedroom cottage with compact kitchen and bath. A true antique from 1850, the unit is renovated but remains quintessential Old Cape Cod. Private laundry, private yard, and walking access to Arey’s Pond 350 yds down private path. A Zen getaway for a couple looking to relax in an ideal Orleans location. Very close to Nauset Beach, Orleans, Chatham, and great dining. A super place to vacation. Updated photos to be posted soon!brThe spacebrVery cute King bedroom studio cottage. smallest and cutest bathroom ever, and a small galley kitchen, plenty of room to make morning coffee, prepare breakfast, or cook dinner. 350yd walk to Areys Pond, deeded access via private path. Walk around back for access to full laundry in the basement.brGuest accessbrGuests have exclusive access to the cottage and access to Arey’s Pond. The property has another rental, a 3 BR antique home that can be rented with the cottage or separately. Both units have privacy and are separated by a new board fence. There are some common areas outdoors as well. Cottage has a beautiful new outdoor shower as well. There is a separate private yard at the cottage with a firepit, grill, and plenty of room outside to sit and relax!! The path to Arey’s Pond is between 350 and 400 yds long from the house to the water’s edge. It is not a beach per se but does allow direct saltwater access for boating, paddle boarding and kayaking. The owners live nearby and have a boat and a mooring so there may be a possibility to arrange a boat ride if you’d like to see the area from the water. Feel free to reach out and ask questions!brOther things to notebrThere is a very friendly yellow lab at the neighboring property, and he may stop by to say “hello”! Please let us know if you do not want to see him.

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$481.65

/ Nightly

Private Vacation Home

1850 Orleans Antique Home with path to Arey’s Pond

Orleans, Massachusetts, United States

Make memories at this private family and pet-friendly 3 BR Orleans antique Cape Cod home with access to Arey’s Pond. Kayak and paddle-board directly to Little Pleasant Bay and beyond. The property was once home to the town pub on Old County Road en route to Orleans. Enjoy the wrap-around 3 season porch. Antique home with bath and other renovations just completed for the 2023 rental season. We want to share this unique property with those who appreciate the history. Please ask questions!brThe spacebrThis is a very authentic antique Cape Cod home. The rooms are small, the stairs are steep, but the baths and kitchen have some updates to add a modern touch to help you enjoy your stay. The tilt top game console on the 3 season porch offers 3505 retro video games, the 350 yd path out back leads right to Arey’s Pond, and the location is super private and couldn’t be better, honestly! We hope you’ll enjoy your stay and return time and time again to OLD Cape Cod!brGuest accessbrThe property has another rental, a 1 BR cottage that can be rented with the main house or separately. Both units have privacy and are separated by a new board fence.brGuests will access the entire house with fenced back yard suitable for dogs. There is a path to Arey’s Pond which is not a beach per se but does allow direct saltwater access for boating, paddle boarding and kayaking. The owners live nearby and have a boat and a mooring so there may be a possibility to arrange a boat ride if you’d like to see the area from the water. Feel free to reach out and ask questions! The path is between 350 and 400 yds long from the house to the water’s edge.brOther things to notebrThere is a very friendly yellow lab at the neighboring property, and he may stop by to say “hello”! Please let us know if you do not want to see him

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Bath

Sleeps

$543.01

/ Nightly

Private Vacation Home

Gray Gables | House in Orleans

Orleans, Massachusetts, United States

Summary:brbrGray GablesbrbrbrbrThe Space:brbrbWhat We Love/b Classic Cape Cod charm and a convenient location within walking distance to nearby natural landmarks are yours at this historic, 1840 home. Nestled on over an acre of land set away from the main road, the home offers an abundance of peace and solitude for your stay. The property backs up to 33 acres of conservation land that features walking trails around two ponds. A good walk down to the end of the road will bring you to Nauset Inlet where beautiful vistas are waiting to award your trek. Nauset and Skaket Beaches are also within easy reach of the home. Two gigantic shade trees provide a pleasant setting for outdoor gatherings, with yard games provided for added entertainment. The six-person dining table on the deck sets the stage for alfresco meals. When you're ready to explore a little, you'll find East Orleans eateries, downtown Orleans, and access to the Cape Cod Rail Trail all within a two-mile radius. The inviting interior exudes a homey ambiance, with traditional decor and original features accenting the home's historic style. The massive full kitchen boasts a full suite of updated stainless steel appliances to help you handle family-style feasts with ease. A smart TV and board games are ready to welcome additional home entertainment in the living room. bHouse Rules/b Check-in time: 4:00 PM Check-out time: 10:00 AM All guests shall abide byour good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises.

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$607.17

/ Nightly

Private Vacation Home

West-facing pure waterfront home in Orleans, overlooking Arey's Pond

Orleans, Massachusetts, United States

Summary:brbrArey's Pond PointbrbrbrbrThe Space:brbrKayakers and nature lovers take note! This four-bedroom, two-bathroom house sits on 2+ waterfront acres in Orleans, offering extraordinary privacy with exquisite water views of historic Arey's Pond, part of Pleasant Bay. (Please note, this is a saltwater pond.) The adjoining 11+ acres of conservation land let you leave the crowds behind. Nauset and Skaket Beaches and a local bike trail are all around four miles away via local roads. Even better, two freshwater swimming lakes are within a mile on quiet lanes. This is a great backroad area for walking, biking, and enjoying nature, yet it's convenient to downtown Orleans and Chatham with their great shops and restaurants. There's also convenient access to Arey's Pond, which connects to Pleasant Bay (prime water for sailing), if you provide your own watercraft. The house offers the easy, indoor-outdoor flow of a classic summer home. When you're having a relaxing dinner on the porch after a day at the beach, you'll know what makes Cape Cod so special. The entrance opens up into a hallway, with a tiled kitchen on your left offering all the appliances, cookware, and utensils you need. After preparing a memorable feast, enjoy it in the dining area while indulging in the view of the pond and lively conversation together. The screened porch adjacent to the living room and dining area serves as an excellent alternative. Few things compare to great food while appreciating the westerly breezes and watching the sun go down. The bathrooms were updated in recent years yet remain in perfect keeping with the classic style of the house. This first-floor bathroom includes a vanity and walk-in shower. The first floor hosts two bedrooms, with one featuring a king and the other with two twin beds. The second floor boasts an additional two bedrooms, with one also featuring a king and the other two twins. The twin bedroom even has a writing desk, in case inspiration strikes while observing the pond. The bathroom in the hallway has a tub and a shower, as well as a single-sink vanity. The living room and dining areas have premium views of the pond and sunsets. Take advantage of the sofa and armchairs to relax while viewing your favorite shows on the 42-inch TV before turning in for a blissful night's rest. bTHINGS TO KNOW/b Please note this home requires a seven-night minimum stay from late June through early September. There is a mini-split downstairs and a window AC unit upstairs.

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Bath

Sleeps

$489.03

/ Nightly

Private Vacation Home

2nd floor Cottage, Oceanview, Deck, Shared Grill, & Outdoor Shower

Orleans, Massachusetts, United States

Summary:brbrNauset Beach DreambrbrbrbrThe Space:brbrJust steps from Nauset Beach, this upper-level Cape Cod cottage offers a relaxed, walkable home base for an easy family vacation. Skip beach parking and fees — enjoy morning swims, midday breaks, and peaceful early strolls along the shore whenever you like. The home is comfortable and well cared for, featuring classic Cape Cod charm with original wooden cabinetry, a practical eat-in kitchen, and a bright living room with cozy seating and Apple TV for streaming. Guests also enjoy access to the shared patio and yard, perfect for unwinding after a day at the beach. Beach towels, chairs, family games, and standard bath linens are provided to make your stay easy and enjoyable. Built by hand by our father and grandfather, this family home has welcomed generations of summer memories. We hope you experience the same Cape Cod magic during your stay. Conveniently located near Orleans shops, dining, grocery stores, kayak and bike rentals, and the Cape Cod Rail Trail (10–15 minute drive). Easy access to Wellfleet, Hyannis, Skaket Beach, Crystal Lake, and more. Please note: The upper level is part of a property that also includes a separate lower-level apartment with its own private entrance. Both units can be rented together for larger or multi-generational groups. bHouse Rules/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.

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Sleeps

$589.78

/ Nightly

Private Vacation Home

Two-story home w/new kitchen, washer/dryer, large yard, & pool table

Orleans, Massachusetts, United States

Summary:brbrBarley BreezebrbrbrbrThe Space:brbrEscape to this beautiful and private Cape Cod retreat in Orleans, MA, where tranquility meets adventure just steps from Pochet Bay. This charming two-story house is the perfect spot for a family vacation, offering easy access to some of the best beaches in the area. Nature lovers will appreciate the scenic waterfront paths nearby, ideal for bird watching and enjoying the stunning coastal views. Inside, the home boasts a delightful blend of hardwood floors and nautical decor, creating a warm and inviting atmosphere. Each room is equipped with air conditioning to ensure your comfort during your stay. The newly remodeled kitchen, completed in 2025, is a culinary delight, featuring a lobster pot for preparing fresh seafood. Gather around the dining table indoors or step outside to the furnished deck for an al fresco dining experience under the stars. For entertainment, the living area features a wall-mounted flat-screen TV, while a cozy den and a basement with a pool table provide additional options for relaxation and fun. Outdoor enthusiasts will love launching kayaks or canoes just down the road into Pochet Bay, where you can explore the sandy shores of Pochet Island and hike scenic trails. Downtown Orleans is just a short drive away, offering a variety of restaurants, shops, and art galleries to explore. Don't miss the chance to charter fish at Rock Harbor, watch the sunset at Skaket Beach, or bike through Nickerson State Park and the Cape Cod Rail Trail. With a range of amenities including a washer/dryer, internet, and a gas grill, this Cape Cod retreat has everything you need for a memorable vacation. Book your stay today and experience the best of Cape Cod! bThings to Know/b Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. Free high-speed WiFi Outdoor shower available Includes beach towels and chairs. Please note there's no central A/C, but A/C units are installed in every bedroom. Access and special features for guests with limited mobility including a first-floor suite.

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Sleeps

$797.76

/ Nightly

Private Vacation Home

Quiet home near Pilgrim Lake with deck, W/D, AC, games, & large yard

Orleans, Massachusetts, United States

Summary:brbrGreat White Cape EscapebrbrbrbrThe Space:brbrEscape to the picturesque town of Orleans, and unwind in this spacious house close to the Pilgrim Lake Recreation & Conservation Area. Ideal for families or groups, this Cape Cod retreat offers a plethora of amenities, including a washer/dryer, central AC, and internet access, ensuring a comfortable and stress-free stay. Step outside onto the deck or patio, complete with cozy furniture and a gas grill, perfect for enjoying outdoor meals or basking in the sun. Just a short walk to Pilgrim Lake, this home is a haven for beach lovers and water enthusiasts looking to explore nearby beaches or try activities like swimming and stand-up paddleboarding. A paddleboard along with two sea kayaks are available for guest use. Inside, the house features a well-equipped kitchen with modern appliances, a welcoming living room with a TV, and multiple levels providing ample space for relaxation. The twin bedroom upstairs features the longer twin XL size beds, which can be positioned together to create a third king bed. Whether you're unwinding after a day of exploring or curling up with a good book from the selection provided, this home offers everything you need for a memorable vacation. Conveniently located near restaurants, shops, and local attractions such as Skaket Beach, Nauset Beach and the town of Chatham, there's plenty to see and do during your stay. Whether you're interested in beachcombing, bird watching, or simply relaxing by the ocean, this charming location caters to all interests. Book your stay at this lovely house and start planning your Cape Cod getaway today! 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.

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Sleeps

$816.68

/ Nightly

Private Vacation Home

Cozy home close to the beach with deck, porch, W/D, & foosball table

Orleans, Massachusetts, United States

Summary:brbrPochet EscapebrbrbrbrThe Space:brbrNestled in the charming town of Orleans, MA, this beautiful house is the perfect retreat for your next vacation. With a spacious porch and deck offering stunning views, you can relax and unwind in style. The foosball table provides entertainment for all ages, while the cozy interior is equipped with all the amenities you need for a comfortable stay. Step inside to find a well-equipped kitchen with a dining table for family meals, and a comfortable living room where you can kick back and watch TV. The house features multiple levels, providing privacy and space for everyone in your group. With one queen bed and three full (double) beds, there’s plenty of room for everyone to rest and recharge. Just steps from the door, you'll find access to outdoor activities like stand-up paddleboarding and beachcombing. Explore the nearby village, stroll along the ocean, or dine at local restaurants offering fresh seafood. For those seeking adventure, there are plenty of opportunities for boating, fishing, kayaking, and more. Whether you're seeking a peaceful retreat or an action-packed getaway, this house in Orleans has something for everyone. Book your stay now and create unforgettable memories on Cape Cod! 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.

4

Bed

5

Bath

8

Sleeps

$821.44

/ Nightly

Private Vacation Home

Charming home steps to beach, includes 2 full units with patio, grill, & views

Orleans, Massachusetts, United States

Summary:brbrNauset Beach GetawaybrbrbrbrThe Space:brbrNauset Dream – Two-Unit Family Retreat This two-unit Cape Cod property includes both the upper-level home and a private lower-level apartment, making it ideal for extended families or groups who want to stay together while enjoying separate living spaces. Each unit has its own entrance, living area, eat-in kitchen, and washer/dryer for convenience and privacy. The units are not connected internally; guests move between them via a short, easy outdoor path. Just steps from Nauset Beach, you can skip parking and fees, enjoy morning swims, take midday breaks, or head out for spontaneous beach strolls. Early mornings are especially peaceful, perfect for a quiet visit to the shore before the crowds arrive. The interiors feature classic Cape Cod charm with original wooden cabinetry and traditional layouts. Both living areas include Apple TV for streaming with your own accounts. A rinse area with a showerhead is available for washing off sand (not a fully private shower). Standard bath linens, extra beach towels, chairs, and games are provided, and guests can enjoy the shared patio with a gas grill for casual outdoor meals. Built by hand by our father and grandfather, this family home has been cared for over generations. We grew up here and now share it with our own children, hoping you feel the same Cape Cod magic. Conveniently located for exploring Orleans and the surrounding Cape—ice cream shops, dining, grocery stores, kayak and bike rentals, and the Cape Cod Rail Trail are all within 10–15 minutes. The property is also well positioned to visit Wellfleet, Hyannis, Skaket Beach, Crystal Lake, and other local favorites. Perfect for families and multi-generational groups, this retreat balances privacy, comfort, and an unbeatable location. 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.

5

Bed

2

Bath

10

Sleeps

$519.02

/ Nightly

Private Vacation Home

Skaket Beach escape: Corner-lot home with big yard - walk to Warm Bayside Shore

Orleans, Massachusetts, United States

Summary:brbrNamskaket RetreatbrbrbrbrThe Space:brbrNestled in the charming town of Orleans, MA, this delightful three-bedroom house offers the perfect blend of quiet privacy and convenient access to the stunning bayside shores. Just a short stroll from the pristine sands of Skaket Beach, this home is ideal for families seeking sun-soaked days filled with swimming and exploring tidal pools. Perched on a spacious corner lot, the property features a brand-new kitchen and a thoughtful layout, with a master suite on one side and two guest bedrooms on the other, ensuring comfort and convenience for all. Inside, the welcoming living area invites relaxation with its comfy seating arrangement, including a sofa, love seat, and armchair. Enjoy movie nights on the 50” smart TV, equipped with cable and a DVD player, or curl up in the sunny reading nook with a good book. The well-equipped kitchen boasts brand-new stainless steel appliances, perfect for whipping up delicious meals. Gather around the dining table for six or perch at the counter for two while dinner simmers. Step outside onto the large deck that overlooks the backyard, an ideal spot for morning coffee or evening barbecues on the gas grill. With the provided beach gear, including chairs, toys, and an umbrella, you can easily pack up for a day at the beach. Additional family-friendly amenities, such as a Wii, video games, and children's books, ensure that everyone has something to enjoy. Located just a mile from the town center, you can explore local attractions like the Hog Island Beer Company for great food and live music. Nauset Beach is also a quick drive away, offering more opportunities for sun and surf. Whether you're looking to relax or embark on outdoor adventures, this Orleans retreat is the perfect home base for your Cape Cod getaway.

Bed

Bath

Sleeps

$477.42

/ Nightly

Private Vacation Home

Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail

Orleans, Massachusetts, United States

Summary:brbrThe Salty OnebrbrbrbrThe Space:brbrAround the corner from the Cape Cod Rail Trail and near Skaket Beach, this beautifully renovated 4BR/2BA classic home is the perfect bayside retreat. Find your bliss in the manicured yard, complete with a cookout-ready stone patio. Coastal colors and fine furnishings adorn the spacious interior. The charming dining room invites memorable family meals beside a gas fireplace. LIVING AREAS The light-filled living room features a soothing color palette. Recline on a plush sofa and two armchairs and find your favorite shows on the 50” TV. A selection of DVDs, books, and games expand your entertainment options. KITCHEN & DINING Prepare your favorite foods in the modern kitchen, outfitted with a full suite of appliances, and fully stocked with all the gadgets you might need. Ample counter space makes it easy to prepare ingredients, and the breakfast nook seats six. The window-lined dining room has a table for eight and a gas fireplace. Share special meals by the light of a chandelier. BEDROOMS & BATHS This home sleeps up to eight guests in between the four bedrooms and a bonus area. The bedrooms are located on the second floor. Make yourself at home in the tranquil master bedroom, detailed with a queen-size bed and a flat-screen TV. The second and third bedrooms feature comfy queen-size beds, while the fourth guest room has a full-size bed. Two twin-size beds await in the bonus area. The guest bathroom on the second floor is appointed with a double vanity and a tub/shower combination. A sparkling walk-in shower rounds out the bathroom on the main floor. OUTDOOR AREAS The oversized yard is the perfect for lawn games or simply relaxing in the shade. Make use of the gas grill and dine alfresco at the table for four. An outdoor shower is handy after fun-filled days at the beach. EXTRA AMENITIES & MORE DETAILS Guest amenities include complimentary Wi-Fi, a washer/dryer, and parking for four cars in the driveway. Please note the bonus area is adjacent to a stairwell, and may not be suitable for small children. THE LOCATION Pedal to the Cape Cod Rail Trail in 0.2 miles; this paved and picturesque 25-mile pathway runs from South Dennis to Wellfleet and travels through the heart of Orleans. Skaket Beach is less than a mile from home. Or visit the Cape Cod National Seashore, only a 5-mile car ride away. Walk to The Jailhouse Tavern in 10 minutes for dinner and live music. Make a reservation at Abba and dine on inventive cuisine, or try out the tasty dishes at The Beacon Room —both just a 10-minute walk from your door.

4

Bed

2

Bath

8

Sleeps

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