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

Oak Bluffs Hotel Guide - Hotels with 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 Pool

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Oak Bluffs hotels with a pool

A two-story house with a stone facade, a covered patio, and a well-maintained garden.
An outdoor patio area with a fire pit, seating, and a pool.
A spacious living room with a fireplace, comfortable seating, and large windows.

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

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
€3,230
includes taxes & fees
25 Sept - 26 Sept
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 large, multi-story building with a balcony on the second floor.
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.

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.
€370
includes taxes & fees
9 Sept - 10 Sept
Mansion House Inn And Spa
A poolside area with lounge chairs and a table.
A reception area with a black leather chair, a reception desk, a television, and a wall with a map display.
A dining area with multiple tables and chairs, a kitchen area with appliances, and a television displaying a logo.
A covered outdoor area with a pool, red chairs, and a table with a bowl.

3. 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.
€139
includes taxes & fees
31 Aug - 1 Sept
Admiralty Inn & Suites - a Red Collection Hotel
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.

4. 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.
€153
includes taxes & fees
9 Sept - 10 Sept
Falmouth Inn
An indoor swimming pool with clear blue water, surrounded by blue lounge chairs and a tiled floor.
A reception desk with a floral arrangement in a green vase, a marble wall with "HOTEL CAP" signage, and a white counter.
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.

5. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
€133
includes taxes & fees
7 Sept - 8 Sept
Iris Hotel Cape Cod
A swimming pool with blue lounge chairs and a stone building in the background.
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.
A cozy room with a grey sofa, a wooden bench, and a tray with a plant.

6. 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.
€214
includes taxes & fees
2 Sept - 3 Sept
Lamberts Cove Inn
A large, multi-story house with a covered porch and a well-maintained lawn.
A hotel room with two beds, a large window, a flat-screen TV, and a painting on the wall.
A neatly arranged bedroom with a bed, pillows, a vase, and a lamp.
A modern bathroom with a wooden vanity, a round mirror, and a glass shower enclosure.

7. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
€203
includes taxes & fees
7 Sept - 8 Sept
Shore Haven Inn
A swimming pool with sun loungers and umbrellas, surrounded by large windows and wooden beams.
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.
A staircase with wooden railings and a lamp on a side table.

8. 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.
€186
includes taxes & fees
22 Sept - 23 Sept
Inn on the Square
A bathroom with a white sink, a toilet, a shower with a glass-enclosed tub, a round mirror, and a shelf with toiletries.
A Mariner Motel sign with a vacancy notice, surrounded by vibrant flowers.
A bedroom with a bed, bedside tables, a chair, a desk, and a painting of a beach scene.
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.
€136
includes taxes & fees
10 Sept - 11 Sept
Mariner Motel
A swimming pool with lounge chairs, a building with a balcony, and trees in the background.
A patio area with Adirondack chairs and a view of a lake surrounded by trees.
A hotel room with two beds, a large window, and a view of the outdoors.
A reception area with a wooden ceiling, a display of brochures, a white chair, and a view of greenery outside.

10. Green Harbor Waterfront Lodging

Green Harbor Waterfront Lodging
East Falmouth
  • Seasonal waterfront pool creates summer magic at this Cape Cod retreat with a garden terrace.
€166
includes taxes & fees
31 Aug - 1 Sept
Green Harbor Waterfront Lodging
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

Inn on the Square

Inn on the Square

8/10 Good
"The only reason I didn't give it a 5 Star was the surprise that the second floor of the other building did not have an elevator. Seniors here with heavy bags struggled. Walkable to town."
Donald 1-night trip
Posted 16 hours ago
Inn on the Square
Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"Happy to stay there and I will be back again"
Anna Kanichada 1-night trip
Posted 1 day ago
Sea Crest Beach Resort
Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"The room was excellent! It was very clean and well maintained. The staff was friendly and extremely helpful considering we arrived very late in the evening."
Mitzi 1-night trip
Posted 5 days ago
Iris Hotel Cape Cod
Faraway Martha's Vineyard

Faraway Martha's Vineyard

8/10 Good
"I enjoyed my stay in the Chappy House – Room 409, a suite with its on entrance from the outside. It was very well appointed and similar to a spacious one bedroom apartment without the kitchen. Must be capable of maneuvering stone pathways and steps to access it. Very nice for a long-term stay. I’d be interested in purchasing one! (Luxury vinyl plank flooring needs repairing in one hallway spot — barely noticeable.) 🙂"
Fred 1-night trip
Posted 6 days ago
Faraway Martha's Vineyard

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: Hotel located near Cape Cod Beaches. Provides a snack bar/deli, an indoor pool and free self parking. Pequot Hotel: Hotel, 2-minute walk from Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool and a private beach. Morgan Hotel: Hotel located near Cape Cod Beaches. Offers daily, a pool and free self parking. The Island Inn on Martha's Vineyard: Hotel, 1-minute walk from Main Street Hyannis. Offers free self parking, a seasonal outdoor pool and flat-screen 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, Oak Bluffs Harbor and Oak Bluffs Ferry Terminal. 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.