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

Oak Bluffs Hotel Guide - Hotels with Pool in Oak Bluffs, Massachusetts

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Check availability on Oak Bluffs Hotels with Pool

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Oak Bluffs hotels with a pool

A swimming pool with a pergola and outdoor seating area.
A two-story house with a stone facade, a covered patio, and a well-maintained garden.
A spacious living room with a fireplace, comfortable seating, and large windows.
A house with a well-maintained lawn and a stone pathway leading to the entrance.

1. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
€3,392
includes taxes & fees
12 Oct - 13 Oct
Beautiful Estate with salt water pool & pond with kayaks
An indoor swimming pool with clear lane markings, tiled walls, and a ceiling with recessed lighting.
A balcony with a table and chairs, overlooking a marina with boats and a distant shoreline.
A marina with boats docked along the shore, surrounded by greenery and a sandy beach.
A large, multi-story building with a balcony on the second floor.

2. 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.
€186
includes taxes & fees
2 Nov - 3 Nov
Mansion House Inn And Spa
A poolside area with lounge chairs, a wooden deck, and a pool.
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.
A spacious lobby with a reception desk, a large sofa, and a chandelier.

3. 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.
€245
includes taxes & fees
1 Nov - 2 Nov
Faraway Martha's Vineyard
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.

4. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
€186
includes taxes & fees
13 Oct - 14 Oct
Shore Haven 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 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.
A spacious living area with a dining table, sofas, and a view of the sea.

5. Harbor View Hotel

Harbor View Hotel
Edgartown
  • Seasonal harbor-side pool escape offers refreshing coastal views and luxury poolside cocktail service.
€315
includes taxes & fees
25 Oct - 26 Oct
Harbor View Hotel
An aerial view of a resort with a pool, beach area with umbrellas, and a large building with a covered deck.
A row of white lounge chairs with blue cushions, arranged under a white canopy, overlooking the sea.
A beachside seating area with blue umbrellas and lounge chairs.
A restaurant with tables set for dining, overlooking a beach.

6. The Club at New Seabury

The Club at New Seabury
New Seabury
  • Splash into poolside bliss at this Cape Cod resort with cabanas, loungers, and two vibrant bars.
€151
includes taxes & fees
1 Nov - 2 Nov
The Club at New Seabury
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.
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.
Outdoor seating with tables and chairs, covered by green umbrellas, and a sign for a breakfast and lunch place.
A large, two-story building with a stone facade, a prominent sign reading "Inn on the Square," and a patio area with outdoor seating.

7. 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.
€176
includes taxes & fees
21 Oct - 22 Oct
Inn on the Square
A swimming pool with blue lounge chairs and a stone building in the background.
A restaurant with wooden flooring, high ceilings, and large windows. Tables are set with chairs and centerpieces.
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.

8. 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.
€277
includes taxes & fees
11 Oct - 12 Oct
Lamberts Cove Inn
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 reception desk with a floral arrangement in a green vase, a marble wall with "HOTEL CAP" signage, and a white counter.

9. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
€132
includes taxes & fees
1 Nov - 2 Nov
Iris Hotel Cape Cod
A poolside area with lounge chairs and a table.
A dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.
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 hotel room with two beds, a desk, and a chair.

10. 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.
€126
includes taxes & fees
1 Nov - 2 Nov
Admiralty Inn & Suites - a Red Collection Hotel
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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

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 17 hours ago
Harbor View Hotel
Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel

8/10 Good
"Pillows were not good. Place was dated with a great continental breakfast!"
Stephanie 1-night trip
Posted 19 hours ago
Admiralty Inn & Suites - a Red Collection Hotel
Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"Good location"
Mary 1-night trip
Posted 2 days ago
Iris Hotel Cape Cod
Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"We loved our stay at the Sea Crest. The woman at the front desk was enormously helpful and kind during our stay, making sure we had everything we needed. Gorgeous view from the room, beautiful beach. If only it was warm enough to swim in the ocean, it would have been perfect."
Deborah 1-night trip
Posted 2 days ago
Sea Crest Beach Resort

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.