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

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Check availability on Oak Bluffs Hotels with Pool

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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 large, multi-story building with a balcony on the second floor.
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.
฿5,832
฿7,010 total
includes taxes & fees
2 Nov - 3 Nov
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.
An outdoor patio with a bar area, seating, and string lights.
A bedroom with a large bed, a view of the outdoors through sliding glass doors, and a balcony with a white railing.

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.
฿7,855
฿9,212 total
includes taxes & fees
1 Nov - 2 Nov
Faraway Martha's Vineyard
A waterfront hotel with a pool, outdoor seating, and a view of the water.
A sandy beach path leading to the ocean, surrounded by sparse vegetation.
A marina with multiple boats docked, surrounded by residential buildings with balconies and a well-maintained lawn.
A spacious room with a dark blue sofa, white walls, and large windows offering a view of a building and a grassy area.

3. The Harborside Inn

The Harborside Inn
Edgartown
  • Float in blissful style at a seasonal outdoor pool, where relaxation meets Martha's Vineyard magic.
฿15,978
฿17,847 total
includes taxes & fees
7 Nov - 8 Nov
The Harborside Inn
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.

4. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
฿9,818
฿11,845 total
includes taxes & fees
25 Oct - 26 Oct
Harbor View Hotel
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.
A staircase with wooden railings and a lamp on a side table.
Outdoor seating with tables and chairs, covered by green umbrellas, and a sign for a breakfast and lunch place.
A hotel room with a large bed, a sitting area with a chair and a table, a bathtub, and a framed picture on the wall.

5. Inn on the Square

Inn on the Square
Falmouth
  • Sun-drenched days await at the indoor pool retreat where year-round swimming creates holiday bliss.
฿5,044
฿6,618 total
includes taxes & fees
25 Oct - 26 Oct
Inn on the Square
A poolside area with lounge chairs and a table.
A room with two beige armchairs, a patterned carpet, a large window with a view of buildings, and a ceiling with recessed lighting and a smoke detector.
A covered outdoor area with a pool, red chairs, and a table.
A dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.

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.
฿3,776
฿4,724 total
includes taxes & fees
1 Nov - 2 Nov
Admiralty Inn & Suites - a Red Collection Hotel
A large, multi-story house with a covered porch and a well-maintained lawn.
A neatly arranged bedroom with a bed, pillows, a vase, and a lamp.
A hotel room with two beds, a large window, a flat-screen TV, and a painting on the wall.
A modern living room with a wicker chair, a round coffee table with a vase, and a sofa with patterned cushions.

7. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
฿5,952
฿6,990 total
includes taxes & fees
19 Oct - 20 Oct
Shore Haven Inn
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 lobby with striped armchairs, a TV, a reception desk, and a blue wall.
A modern hotel room with a curved ceiling, a large bed, a flat-screen TV, a desk with a chair, and a bathroom with a mirror and sink.

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.
฿4,330
฿5,627 total
includes taxes & fees
15 Oct - 16 Oct
Falmouth Inn
An indoor swimming pool with clear blue water, surrounded by white lounge chairs and a tiled floor.
A modern bar area with a white countertop, blue bar stools, and a wooden accent wall.
A hotel reception area with a wooden reception desk, a red chair, and a wall sign welcoming guests to the Patriot State.
A fire pit surrounded by wicker furniture with blue cushions, set on a stone patio.

9. Hampton Inn Cape Cod Canal

Hampton Inn Cape Cod Canal
Buzzards Bay
  • Escape to a year-round pool paradise with cosy loungers at this Art Deco canal hotel.
฿4,376
฿5,009 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Cape Cod Canal
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 long dining table with a glass centerpiece, surrounded by chairs and a buffet setup.
A cozy living room with a stone fireplace, leather sofas, and a large window with blinds.

10. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
฿4,330
฿4,956 total
includes taxes & fees
1 Nov - 2 Nov
Iris Hotel Cape Cod
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

The Bridgeway

The Bridgeway

8/10 Good
"Our stay was great the only issue was the sleeping arrangements, the room I book said it slept 3 but there was only one bed and a chair so I'm assuming the third person ws meant to be an infant, but it doesn't say that in the description. Even though there was only one bed we still made it work and had a great time. My only suggestion would be for the owners to invest in a roll-away bed and put it in the description that it is only one bed with no other sleeper options available. I would 100 stay again!"
Laken 4-night trip
Posted 4 hours ago
The Bridgeway
Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"Nice stay."
Erin 1-night trip
Posted 21 hours ago
Iris Hotel Cape Cod
Hyannis Plaza Hotel

Hyannis Plaza Hotel

10/10 Excellent
"Property is good the bad is that doesn’t have a microwave in room and others use parking from places around and when I want to park there is no parking and I am paying for this hotel."
Franchesca 2-night trip
Posted 2 days ago
Hyannis Plaza Hotel
Harbor View Hotel

Harbor View Hotel

10/10 Excellent
"Beautiful Hotel and Venue with impeccable amenities. Beautiful water views and outstanding and friendly Staff. Disappointed we were not able to stay longer. Will definitely plan another trip in the near future!"
Marc 1-night trip
Posted 5 days ago
Harbor View Hotel

Frequently asked questions

What are some accommodation options 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: Holiday home located near Inkwell Beach. Features sunloungers, 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, visit 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 the local weather in Oak Bluffs into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 20°C, while the coldest months are February and January, with an average of 3°C. Average annual precipitation for Oak Bluffs is 1192 mm.

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