TOP Hotels with Swimming Pool in Osterville, MA for 2026

Q: What are some accommodation options with pools in Osterville?

Margaritaville Resort Cape Cod : Resort steps from Cape Codder Water Park. Features a children's pool, an indoor pool and a water park. Iris Hotel Cape Cod : Hotel located near Cape Cod Beaches. Offers a snack bar/deli, an indoor pool and free self parking. Sea Crest Beach Resort : Hotel, 2-minute walk from Cape Cod Beaches. Provides a children's pool, a seasonal outdoor pool and a private beach. Uncommoner Hotel by Reverie Boutique Collection : Hotel, 8-minute walk from Main Street Hyannis. Features a seasonal outdoor pool, an indoor pool and 2 bars. Riviera Beach Resort : Hotel, 3-minute walk from Cape Cod Beaches. Offers a children's pool, a seasonal outdoor pool and a private beach.

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 Osterville Hotels with Swimming Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Osterville hotels with a pool

Craigville Beach Inn

Centerville

Splash into beachside bliss with an indoor pool and complimentary beach shuttle service.

₹25,206 total

includes taxes & fees

23 Jul - 24 Jul

Margaritaville Resort Cape Cod

Hyannis

Poolside paradise at this Cape Cod resort with outdoor pools, waterpark, and a lazy river waiting for you.

₹30,009 total

includes taxes & fees

19 Aug - 20 Aug

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Hyannis

Serene indoor pool sanctuary beckons for a relaxing Cape Cod escape after a day of harbour exploration.

₹25,185 total

includes taxes & fees

17 Aug - 18 Aug

Indoor pool, outdoor pool, pool loungers

Holiday Inn Hyannis by IHG

Hyannis

Splash into poolside perfection with dual swimming options and a steamy hot tub escape.

₹21,279 total

includes taxes & fees

2 Aug - 3 Aug

Hyannis Travel Inn

Hyannis

Splash into summer at this Cape Cod oasis with refreshing indoor and outdoor pools.

₹19,465 total

includes taxes & fees

26 Jul - 27 Jul

Hyannis Harbor Hotel

Hyannis

Splash into seaside fun with three distinct pools and a poolside bar steps away from Hyannis Harbour.

₹30,964 total

includes taxes & fees

26 Jul - 27 Jul

Courtyard By Marriott Cape Cod Hyannis

Hyannis

Swim year-round at this spotless indoor pool hotel, steps from Hyannis Harbour.

₹28,171 total

includes taxes & fees

16 Aug - 17 Aug

Indoor pool, seasonal outdoor pool, pool loungers

Aiden by Best Western Cape Cod - West Yarmouth

West Yarmouth

Swim in serenity at a beachside oasis with both indoor and seasonal outdoor pools.

₹22,376 total

includes taxes & fees

2 Aug - 3 Aug

View all properties

Choose what matters most at hotels with a pool in Osterville

Breakfast included

4 stars

Top Osterville Hotel Reviews

All Seasons Resort, Trademark Collection by Wyndham

8/10 Good

"Great hotel on the Cape. It was convenient, priced well, the rooms were updated and clean and the swimming pools both inside and out were great. After we left the hotel, my son realized he left his wallet on the nightstand. I called and the woman at the front desk who was working on Friday, July 17th made a special trip to the room, retrieved the wallet and had it waiting for my son when he arrived. Great service from start to finish. Thank you!"

Frequently asked questions

What are some accommodation options with pools in Osterville?

Margaritaville Resort Cape Cod: Resort steps from Cape Codder Water Park. Features a children's pool, an indoor pool and a water park. Iris Hotel Cape Cod: Hotel located near Cape Cod Beaches. Offers a snack bar/deli, an indoor pool and free self parking. Sea Crest Beach Resort: Hotel, 2-minute walk from Cape Cod Beaches. Provides a children's pool, a seasonal outdoor pool and a private beach. Uncommoner Hotel by Reverie Boutique Collection: Hotel, 8-minute walk from Main Street Hyannis. Features a seasonal outdoor pool, an indoor pool and 2 bars. Riviera Beach Resort: Hotel, 3-minute walk from Cape Cod Beaches. Offers a children's pool, a seasonal outdoor pool and a private beach.

What is there to see and do in Osterville?

Explore places such as Cape Cod Beaches while you're in Osterville. Make a point to visit attractions such as Stand Up & Paddle Cape Cod.

When is the best time to book a hotel with a pool in Osterville?

Taking the local weather in Osterville into account can help you maximise your time at the pool during your trip. 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 Osterville is 1328 mm.

Explore a world of travel with Expedia

More ways to book

Book Hotels with Swimming Pool in Osterville on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Osterville Hotels with Swimming Pool