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
Aug 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Oak Bluffs hotels with a pool

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.
P23,105
P26,720 total
includes taxes & fees
Sep 7 - Sep 8
Mansion House Inn And Spa

2. 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.
P8,119
P10,033 total
includes taxes & fees
Sep 1 - Sep 2
Admiralty Inn & Suites - a Red Collection Hotel

3. Iris Hotel Cape Cod

Iris Hotel Cape Cod
Falmouth
  • Splash into year-round relaxation with an indoor pool retreat at this Cape Cod hotel.
P8,408
P9,622 total
includes taxes & fees
Sep 7 - Sep 8
Iris Hotel Cape Cod

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.
P8,589
P11,066 total
includes taxes & fees
Sep 10 - Sep 11
Falmouth Inn

5. Mariner Motel

Mariner Motel
Falmouth
  • Dive into seaside serenity at this coastal retreat with a sun-drenched pool oasis.
P8,589
P9,829 total
includes taxes & fees
Sep 1 - Sep 2
Mariner Motel

6. Shore Haven Inn

Shore Haven Inn
Falmouth
  • Seasonal outdoor pool offers relaxing aquatic escape surrounded by garden views in this beachside sanctuary.
P13,220
P15,527 total
includes taxes & fees
Sep 10 - Sep 11
Shore Haven Inn

7. 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.
P10,457
P13,414 total
includes taxes & fees
Sep 20 - Sep 21
Inn on the Square

8. Falmouth Heights Motor Lodge

Falmouth Heights Motor Lodge
Falmouth Heights
  • Splashing summer days at this Falmouth hotel's sparkling pool with loungers and beach bars nearby.
P11,678
P13,366 total
includes taxes & fees
Sep 17 - Sep 18
Falmouth Heights Motor Lodge

9. Mariner's Point Resort

Mariner's Point Resort
Falmouth Heights
  • Dive into summer splendor at this private beachfront resort with a seasonal sun-soaked pool area.
P10,849
P12,417 total
includes taxes & fees
Sep 14 - Sep 15
Mariner's Point Resort
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

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 hours ago
Faraway Martha's Vineyard
Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"The staff are amazing and will offer to help in any way they can! The property"
Dorien 3-night trip
Posted 1 day ago
Iris Hotel Cape Cod

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: 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, check out 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 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