A row of colorful, historic houses with a central path.

Hotels with Swimming Pool in Oak Bluffs, Massachusetts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Oak Bluffs Hotels with Swimming Pool

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Oak Bluffs hotels with a pool

An indoor swimming pool with clear lane markings, tiled walls, and a ceiling with recessed lighting.
A marina with boats docked along the shore, surrounded by greenery and a sandy beach.
A balcony with a table and chairs, overlooking a marina with boats and a distant shoreline.
A spacious living room with a large sofa, a chair, and a small table. There are several potted plants and a ceiling fan.

1. Mansion House Inn And Spa

Mansion House Inn And Spa
Vineyard Haven
  • Refreshing indoor pool sanctuary complements rooftop terrace views and a soothing hot tub at this Martha's Vineyard spa retreat.
P10,868
P13,063 total
includes taxes & fees
Nov 2 - Nov 3
Mansion House Inn And Spa
A poolside area with lounge chairs, a wooden deck, and a pool.
A spacious dining area with a long table surrounded by wicker chairs, wooden panel walls, and large windows.
A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.
A spacious lobby with a reception desk, a large sofa, and a chandelier.

2. Faraway Martha's Vineyard

Faraway Martha's Vineyard
Edgartown
  • Dive into poolside bliss with comfy loungers, a hot tub, and a convenient bar for refreshments.
P14,637
P17,167 total
includes taxes & fees
Nov 1 - Nov 2
Faraway Martha's Vineyard
A swimming pool with lounge chairs and umbrellas, surrounded by a building with a balcony and a clear sky.
A deck with a wicker sofa, a table with a bottle of champagne, and a tray of snacks.
A spacious living area with a dining table, sofas, and a view of the sea.
A balcony with a view of the harbor, a dining area with a table and chairs, and a small seating area with a bench and a table.

3. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
P15,247
P18,393 total
includes taxes & fees
Oct 25 - Oct 26
Harbor View Hotel
A swimming pool with blue lounge chairs and a stone building in the background.
A room with a wooden deck, a white dresser, and a window with a view of a yard.
A covered porch with wicker furniture and a vase of flowers.
A restaurant with wooden flooring, high ceilings, and large windows. Tables are set with chairs and centerpieces.

4. Lamberts Cove Inn

Lamberts Cove Inn
Vineyard Haven
  • Escape to a private beachside haven with a seasonal pool, where comfort meets coastal charm and nature's serenity awaits you.
P15,144
P16,916 total
includes taxes & fees
Nov 1 - Nov 2
Lamberts Cove Inn
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.
A large, two-story building with a stone facade, a prominent sign reading "Inn on the Square," and a patio area with outdoor seating.
Outdoor seating with tables and chairs, covered by green umbrellas, and a sign for a breakfast and lunch place.
A staircase with wooden railings and a lamp on a side table.

5. Inn on the Square

Inn on the Square
Falmouth
  • Sun-drenched days await at the indoor pool retreat where year-round swimming creates vacation bliss.
P7,760
P10,456 total
includes taxes & fees
Nov 1 - Nov 2
Inn on the Square
A poolside area with lounge chairs and a table.
A hotel room with a large bed, a sofa, a desk, a TV, and a painting on the wall.
A dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.
A gym with treadmills, a bench, and a mirrored wall.

6. Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel
East Falmouth
  • Dive into year-round aquatic bliss with indoor and seasonal outdoor pools in Cape Cod.
P6,755
P8,482 total
includes taxes & fees
Nov 1 - Nov 2
Admiralty Inn & Suites - a Red Collection Hotel
An indoor swimming pool with clear blue water, surrounded by blue lounge chairs and a tiled floor.
A beach with people sunbathing and swimming, a clear blue sky, and a sailboat in the distance.
A cozy living room with a stone fireplace, leather sofas, and a large window with blinds.
A long dining table with a glass centerpiece, surrounded by chairs and a buffet setup.

7. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
P8,069
P9,235 total
includes taxes & fees
Nov 1 - Nov 2
Iris Hotel Cape Cod
An indoor swimming pool with lounge chairs, a lifeguard sign, and American flags.
An aerial view of a marina with boats, a pier, and a town with houses and buildings.
A bar area with multiple screens displaying sports content, a counter with various bottles, and a seating area with tables and chairs.
A lobby with striped armchairs, a TV, a reception desk, and a blue wall.

8. Falmouth Inn

Falmouth Inn
Falmouth
  • Dive into refreshing comfort with an indoor pool oasis that's perfect year-round at this Cape Cod getaway with beach access.
P8,069
P10,486 total
includes taxes & fees
Oct 12 - Oct 13
Falmouth Inn
A bathroom with a white sink, a toilet, a shower with a glass-enclosed tub, a round mirror, and a shelf with toiletries.
A bedroom with a bed, bedside tables, a chair, a desk, and a painting of a beach scene.
A fenced backyard with a pool, picnic table, and trees.
A building with a sign reading "Mariner Motel" and a garden with various flowers in front.

9. Mariner Motel

Mariner Motel
Falmouth
  • Dive into seaside serenity at this coastal retreat with a sun-drenched pool oasis.
P8,069
P9,235 total
includes taxes & fees
Oct 5 - Oct 6
Mariner Motel
A large, multi-story house with a covered porch and a well-maintained lawn.
A modern living room with a wicker chair, a round coffee table with a vase, and a sofa with patterned cushions.
A hotel room with two beds, a large window, a flat-screen TV, and a painting on the wall.
A modern bathroom with a wooden vanity, a round mirror, and a glass shower enclosure.

10. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
P11,091
P13,026 total
includes taxes & fees
Oct 13 - Oct 14
Shore Haven Inn
View all properties

Choose what matters most at hotels with a pool in Oak Bluffs

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Oak Bluffs Hotel Reviews

Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent
"Honestly, I was pleasantly surprised by how nice and clean it was, and how safe I felt at the property. I read some of the previous reviews and was a little nervous but upon arrival, I was completely at ease. The room was very spacious, updated, clean, and everything was in working order. It had a nicer than usual coffee hot and ion blow dryer. Those are some nice touches. Breakfast was wonderful as well."
sherry 1-night trip
Posted 5 hours ago
Admiralty Inn & Suites - a Red Collection Hotel

Frequently asked questions

What are some accommodations with pools in Oak Bluffs?
Summercamp: Resort located near Inkwell Beach. Offers 3 outdoor tennis courts, a seasonal outdoor pool, and free self parking. MV Surfside Hotel: Vacation home located near Inkwell Beach. Features sun loungers, a pool, and kitchens. Morgan Hotel: Hotel, 2-minute walk from Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool, and a private beach. Pequot Hotel: Offers a snack bar/deli, an indoor pool, and free self parking. The Island Inn on Martha's Vineyard: Provides complimentary wireless internet access, an indoor pool, and televisions.
What is there to see and do in Oak Bluffs?
Surround yourself with nature at Ocean Park and Oak Bluffs Town Beach. During your stay, check out sights such as Circuit Avenue, Flying Horses Carousel, and Oak Bluffs Harbor. The beaches, wineries, and shopping are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Oak Bluffs?
Taking into account the local weather in Oak Bluffs is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 68°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Oak Bluffs is 47 inches.

Explore a world of travel with Expedia