The Best Hotels with a Pool in Osterville, MA from ₩250,443 in 2026

Q: What are some accommodations 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 a 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.

₩387,076 total

includes taxes & fees

Jul 26 - Jul 27

Margaritaville Resort Cape Cod

Hyannis

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

₩460,822 total

includes taxes & fees

Aug 19 - Aug 20

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Hyannis

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

₩381,155 total

includes taxes & fees

Aug 23 - Aug 24

Holiday Inn Hyannis by IHG

Hyannis

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

₩314,282 total

includes taxes & fees

Aug 23 - Aug 24

Hyannis Harbor Hotel

Hyannis

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

₩500,656 total

includes taxes & fees

Aug 23 - Aug 24

Outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas, sun loungers

Hyannis Plaza Hotel

Hyannis

Seasonal Cape Cod escape with a pristine pool oasis surrounded by blooming garden views.

₩420,728 total

includes taxes & fees

Jul 28 - Jul 29

Hyannis Travel Inn

Hyannis

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

₩250,443 total

includes taxes & fees

Aug 23 - Aug 24

Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

Comfort Inn Hyannis - Cape Cod

Hyannis

Splash into relaxation with a serene indoor pool experience and bubbling hot tub retreat.

₩287,835 total

includes taxes & fees

Aug 18 - Aug 19

View all properties

Choose what matters most at hotels with a pool in Osterville

Breakfast included

4 stars

Top Osterville Hotel Reviews

Cape Sands Inn

10/10 Excellent

"Very accommodating and pleasant staff..this was a last minute choice and the hospitality exceeded what i thought it would be!"

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 accommodations 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 like Cape Cod Beaches while you're in Osterville. Make a point to visit attractions like Stand Up & Paddle Cape Cod.

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

Taking into account the local weather in Osterville can help you maximize your time at the pool during your trip. The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 37°F. Average annual precipitation for Osterville is 52 inches.

Explore a world of travel with Expedia

More ways to book

Book Hotels with a Pool in Osterville on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Osterville Hotels with a Pool