Vacation rentals with a fireplace in Oak Bluffs

Guesthouse in Centerville

A charming carriage house with shingle siding is set against a blue sky adorned with fluffy clouds. A black Jeep is parked in front, showcasing the gravel driveway. Lush greenery surrounds the property, enhancing its inviting appearance.

5 out of 5 average rating, 137 reviews

Modern Fireplaced Carriage House with Beach Permit

Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.

4.94 out of 5 average rating, 133 reviews

An open living area features high ceilings with exposed beams, large windows allowing natural light, and a cozy sofa facing a white coffee table. The kitchen and dining space are accessible, creating a welcoming atmosphere for relaxation and gatherings.

Home in Vineyard Haven

Vineyard Haven Walk to Ferry

I love this neighborhood! It is quiet, peaceful, and only a short walk to either Tashmoo Beach or downtown Vineyard Haven and the ferry. The house has plenty of outdoor space with it's own wood fired pizza oven, fire pit, garden and decks. There are nice seating areas near the fire pit, on the lower deck and on the upper deck. Walk through the backyard, down a dirt road and be at the water in five minutes. Beach towels included! Plenty of sliding glass doors and LOTS of light. Vitamix included!

4.97 out of 5 average rating, 105 reviews

An aerial view captures a serene landscape, featuring a home surrounded by lush greenery. A tranquil pond reflects the sky, with dense trees framing the scene, creating a peaceful retreat close to nature.

Home in West Tisbury

Lambert's Cove Retreat, Water view, Beach pass

Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

5 out of 5 average rating, 7 reviews

A series of white shelves is mounted on a wall, displaying an assortment of colorful books and decorative items. Notable elements include a model sailboat, a lighthouse figurine, and a potted plant. A woven light fixture hangs above, casting a warm glow on the arrangement.

Townhouse in Edgartown

Bright townhome with private ponds, pickleball

Beautifully furnished condo is centrally located in a park-like setting. This property is perfect for anyone who loves to explore the outdoors or just relax on the private deck at home. The Sengekontacket Assoc. in Oak Bluffs is a desirable waterfront community easily located off the bike path and on the bus route to town. Private amenities include a freshwater pond just 2-min walk down a quiet road; a large saltwater pond about a 10-min walk to a community dock; and tennis/pickleball courts.

Guest suite in Oak Bluffs

A hallway features a patterned runner rug, leading towards light-filled rooms. Green walls create a soothing backdrop, with doors on either side. A glimpse of hardwood flooring and a vacuum cleaner is visible in the distance, indicating a well-maintained space.

5 out of 5 average rating, 26 reviews

Spacious 1 Bedroom Apt - 3 min walk to the Beach!

A perfect place for 1 -4 people to stay! You will have plenty of room, shared use of a grill, backyard, and outdoor dining area. Location is great - it's only a 3 minute walk to the lagoon/beach, 20 minute walk to the Oak Bluffs harbor, 25 minute walk to downtown Oak Bluffs, and 7 minute drive to State Beach. We also have central AC and heating! The owners live upstairs with two young kids (4 & 6) and a dog. As such, this listing is for early-risers ready to enjoy the island mornings :)

5 out of 5 average rating, 14 reviews

Quaint Roomy Ranch

Enter this light filled and airy home with soaring cedar lined ceilings and an entire southern facing wall of windows. This surprisingly spacious home has enough room for the whole family and more. Kids will love having the bunk room to themselves while parents can enjoy the rest of the living area in peace. Located in a quiet neighborhood, this is a perfect family retreat. Enjoy the expansive deck while you grill lunch or dinner and finish up the evening with s'mores by the fire pit.

4.98 out of 5 average rating, 342 reviews

A wooden deck is shown with outdoor seating, including a table and chairs. Surrounding the deck are blooming rose bushes and lavender plants, adding vibrant colours to the natural landscape. The space is bordered by natural stone and pebbles, leading into a wooded area.

Cottage in West Chop

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

A circle of six wooden chairs is set on a grassy area surrounded by tall evergreen trees. In the center, a fire pit is positioned, providing a cozy gathering space for outdoor relaxation.

4.96 out of 5 average rating, 93 reviews

**Vineyard Vacation Retreat** -3 BR

Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large bedrooms and open concept kitchen/dining/living area accommodate up to 6 people comfortably. A place for you to put your feet up, kick away your worries, and enjoy some rest and relaxation. There is so much to do and explore. The adventure is just starting so make sure to pack up your swimmers, suntan lotion and get out the door. Kick back and relax, you're home.

A hot tub is seen with bubbles gently rising from the surface. The control panel displays a temperature setting of 105°F, allowing for a comfortable soak. Soft blue lights illuminate the water, creating a relaxing atmosphere in the outdoor setting.

5 out of 5 average rating, 23 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

LOCATION LOCATION ✅ Rated Top 5% of Homes ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood ✅ HotTub, Fire Pit, Trails at your door step, perfect for peaceful strolls or energetic hikes through lush landscapes. AND Flexibility, with Every detail curated for comfort and style, you'll feel at home the moment you step inside. Located with the island's natural beauty around you, unwind and reconnect with nature.

4.93 out of 5 average rating, 121 reviews

Home in Woods Hole

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on semi-private road with and ocean view of Vineyard Sound. Renovations completed in mid-July, 2020. Three BR, 2 private attached baths, 1 semi-private bath, fully equipped kitchen, patio with BBQ grill, gas fireplace, cable-TV, WiFi internet, large second-floor deck, a/c.. Close to Vineyard Ferry, bus station and town. Seasonal rent. Please complete a reservation request to determine the rent in effect for your requested dates.

4.93 out of 5 average rating, 40 reviews

Charming Vacation Home in Oak Bluffs.

Escape to our stunning 4-bedroom home near Downtown Oak Bluffs and pristine beaches. Ideal for up to 8 guests, our open-concept layout and cozy bedrooms offer comfort and privacy. Experience a serene retreat with all the amenities you need for a perfect vacation. Book now for an unforgettable stay! Please note: the basement of the listed house is currently occupied. Enjoy the main house's 4 bedrooms, open-concept space, and ideal location near beaches.

Superhost

A welcoming porch is featured with a classic rocking chair positioned beside a vibrant display of blue hydrangeas. The wooden siding of the home and large windows create a cozy aesthetic, surrounded by lush greenery.

4.84 out of 5 average rating, 51 reviews

3 beds, 3 baths 1.5 Miles to Downtown and Beaches!

Attractive Vineyard home located steps from Farm Neck Golf Course and Land Bank walking trails. 1.5 miles to downtown and beaches and right on the bike path! Open spaces with lots of light, cathedral ceilings, mahogany deck, covered porch and outdoor shower. Granite countertops with copper edging and stainless appliances. Walk to Farm Neck Golf Course and Café for breakfast, lunch, dinner or night cap. Bike to the beach or BBQ on the deck.

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Popular amenities for Oak Bluffs fireplace rentals

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Pool

Free parking on premises

Air conditioning

House rentals with a fireplace

Superhost

A modern kitchen showcases custom cabinetry and a spacious island, bordered by elegant tile flooring. A round dining table with woven chairs sits on a circular rug, illuminated by a stylish chandelier. Natural light filters in through large windows, enhancing the inviting space.

4.86 out of 5 average rating, 7 reviews

Katama Coastal Farmhouse- ferry tickets available

MeghanRating, 5 stars7 months ago

The house is in a perfect location to get to town or to the beach. I’d recommend a car or bikes, but it’s roughly a mile walk to town. It comfortably accommodated 5 adults and more adults could have been part of the trip with the amount of space in the house. Diane was accommodating to a late check out with a ferry later in the afternoon.

The exterior of a newly constructed home is presented, featuring a sloped roof and two skylights. A welcoming porch extends across the front, lined with decorative lighting. Green shrubs and a gravel driveway lead up to the entrance, surrounded by trees that enhance the private setting.

4.96 out of 5 average rating, 72 reviews

Newly constructed home with AC , new furniture.

Ana-LuciaRating, 5 starstoday

Wonderful place. Beautiful home, located near oak bluffs and edgartown. Great for families!

5 out of 5 average rating, 12 reviews

Home in Popponesset

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

CarolRating, 5 stars1 month ago

We loved are family stay at Paul & Katie’s home for Easter Week. It is a dream home . The neighborhood was beautiful and walkable, with a peaceful path to a private beach. We enjoyed the shops and restaurants in Mashpee Commons about an 8 minute drive away.

4.98 out of 5 average rating, 42 reviews

Two white Adirondack chairs are positioned on a sandy beach area by Wequaquet Lake, facing calm waters. A swan glides gracefully in the distance, surrounded by greenery. The serene landscape offers a sense of tranquility, ideal for relaxation.

Home in Barnstable

Private Lake Beach | Spectacular Views & Amenities

AndrewRating, 5 stars1 month ago

This is an absolutely beautiful rental and location. Cleanest, most pristine location we have been to. Appliances and bathrooms are glimmering. Host is immediately responsive and kind. 10 out of 10 in all respects.

A comfortable seating area is presented with a light gray sectional sofa, complemented by a patterned area rug. Natural light enters through the window coverings, and a tall green plant adds a touch of greenery. A television is positioned on a wooden stand against the wall.

4.91 out of 5 average rating, 65 reviews

Beach, Shop, Restaurant, Bike path,

BridgetteRating, 5 stars9 months ago

Ana’s place was perfect for our long weekend girl’s trip. The kitchen, grill, and outdoor seating were great for a cookout. We loved walking and biking to Morning Glory Farm for coffee, breakfast, and produce for our day!

Superhost

The exterior of the home features a spacious lawn, surrounded by trees. A patio area is visible, with outdoor seating and a playset in the background. The charming two-story house showcases a shingled façade and large windows that invite natural light.

4.63 out of 5 average rating, 8 reviews

Sea Glenn Flowers renovated pet friendly close to

StaceyRating, 5 stars21 months ago

We loved our stay at Sea Glen Rd! The house was tucked back in the woods and felts very private. The VTA bus stop is right at the start of the road with quick easy access to vineyard haven and Edgartown. Try Mad Martha’s Brewery done the street. Great brews and pizza!

The exterior of a two-unit house is displayed, featuring a central white door framed by two symmetrical windows. Flowering shrubs in vibrant pink and white enhance the landscape, while a gravel yard stretches out in front. The structure is surrounded by trees providing shade.

5 out of 5 average rating, 14 reviews

Walk to downtown Edgartown in a quiet neighborhood

ReneeRating, 5 stars9 months ago

This is my family's second year staying here and we plan to be back. It is walkable to downtown Edgartown, near to the supermarket, relaxing, and well-appointed. The host is super-friendly and attentive, as well as responsive. Looking forward to returning!

5 out of 5 average rating, 27 reviews

A spacious living area features a sectional sofa adorned with decorative pillows, positioned near a fireplace with a large wall-mounted TV above it. The room’s blue walls complement a dining space visible in the background, showcasing a round dining table surrounded by upholstered chairs.

Home in New Seabury

Beach/Dining |Fully Renovated| Fire Pit| King Bed!

SamanthaRating, 5 stars2 weeks ago

A gorgeous house in a great location!! I loved the layout of the house, it was so open and in a big fan of open concept spaces. The bedrooms were also a really great size with lots of room to play for the kids. One thing I was very pleased to find was that while it is technically “three floors” each set of stairs is VERY short, so it doesn’t feel like your climbing a mountain every time you need to get upstairs. The house was extremely clean and wonderfully organized The kids bedroom was FULL of toys for all ages and my daughter loved going through it all. The available high chair and pack n play were also a really convenient and appreciated touch. Lastly, Marianna was SO NICE and incredibly helpful!!! I asked her about the location of some laundry detergent and we realized there was none. She immediately door dashed an entire gallon of detergent to the house without me even asking. So sweet!! I would definitely stay here again!!!

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Apartment rentals with a fireplace

Apartment in East Falmouth

A functional kitchen space is equipped with essential appliances, including a stove, microwave, and toaster. Wooden cabinetry houses various kitchenware. The layout features a countertop with a dish rack and a small step stool beneath. Soft lighting creates a welcoming atmosphere.

4.95 out of 5 average rating, 314 reviews

In-law apt. with all the amenities of Home.

KateRating, 5 stars7 months ago

We had a short but pleasant stay at Gail’s and the in-law apartment was perfect! Check in was easy and the apartment was clean, comfortable, and well-appointed with great snacks! This is a great location for exploring Falmouth and the rest of the Cape and Gail is super friendly and responsive. We hope to stay longer next time!

4.85 out of 5 average rating, 39 reviews

A spacious bed is dressed in white linens with a patterned accent blanket and matching decorative pillows. Light wooden furniture complements the blue walls, and a tall cabinet is positioned nearby, enhancing the room's overall comfort and functionality.

Apartment in Falmouth

Sunshine Beautiful

NicoleRating, 5 starstoday

This place is perfect for 1 or 2 people. Close to town by car but quiet. Big yard, super clean, very quiet.

An outdoor patio area is surrounded by lush gardens featuring blooming flowers and greenery. Two blue chairs are positioned near a table underneath a large umbrella, providing a shaded space for relaxation. The backdrop includes a well-maintained building with multiple glass doors.

Apartment in Aquinnah

4.7 out of 5 average rating, 23 reviews

Quiet & Serene in Aquinnah

StephanieRating, 5 stars9 months ago

Lovely stay here in this pristine part of the Vineyard. Expect shabby chic. Would definitely stay again. The location cannot be beat and the hosts were very kind and accommodating!

4.91 out of 5 average rating, 127 reviews

A wooden staircase leads down through lush greenery towards a serene lake. Vibrant flowers in a planter add a touch of color to the natural landscape, while tall trees frame the scene, creating a peaceful atmosphere.

Apartment in Sandwich

Spacious 2 Bedroom Lakefront Suite

AnyiRating, 5 stars9 months ago

Our recent stay at Dori's was a blissful escape for our family. Our five-month-old loved the serene and peaceful atmosphere, which was even more charming than the pictures suggested. It was exactly what we needed to unwind as new parents. Dori was incredibly welcoming and helpful, going above and beyond to ensure our comfort. She offered to order and pick up for us some takeout when we were caught in a thunderstorm, and lent my dad a jacket since it’s pretty cool during the morning than we expected. It’s a wonderful Airbnb but it’s Dori that made our trip truly special.