TOP Hotels with Swimming Pool in Osterville, MA for 2026

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

Iris Hotel Cape Cod : Hotel located near Cape Cod Beaches. Features a snack bar/deli, an indoor pool and free self parking. Sea Crest Beach Resort : Hotel, 2-minute walk from Cape Cod Beaches. Offers a children's pool, a seasonal outdoor pool and a private beach. Bayside Resort Hotel : Hotel, 15-minute walk from Main Street Hyannis. Provides a seasonal outdoor pool, an indoor pool and 2 pool bars. Margaritaville Resort Cape Cod : Resort located near Cape Cod Beaches. Features a children's pool, an outdoor pool and a water park. AutoCamp Cape Cod : Hotel, 2-minute walk from Cape Cod Beaches. Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access.

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Our top choices for Osterville hotels with a pool

Blue Rock Resort

South Yarmouth

Enjoy peaceful days by a seasonal outdoor pool surrounded by manicured gardens at this tranquil Cape Cod retreat.

₹10,742 total

includes taxes & fees

8 Jun - 9 Jun

2 indoor pools, seasonal outdoor pool, pool umbrellas, pool loungers

Charm on Main by Ocean Edge

Sea Pines

Escape to a white sand beach retreat with a seasonal outdoor pool, sun loungers, and umbrellas just steps from the shore.

₹21,181 total

includes taxes & fees

11 Jun - 12 Jun

Travelodge by Wyndham Cape Cod Area

West Dennis

Splash into Cape Cod holiday bliss at this outdoor pool sanctuary with comfy rooms nearby beaches.

₹7,796 total

includes taxes & fees

7 Jun - 8 Jun

Dennis Port Surf Club (Boutique Hotel)

Dennis Port

Seasonal outdoor pool offers refreshing oceanside swims after coastal adventures.

₹13,971 total

includes taxes & fees

8 Jun - 9 Jun

GuestLodge

West Dennis

Refreshing pool oasis awaits at Cape Cod motel with aquatic fun just steps from beaches.

₹7,943 total

includes taxes & fees

7 Jun - 8 Jun

Hyannis Travel Inn

Hyannis

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

₹12,133 total

includes taxes & fees

8 Jun - 9 Jun

Sesuit Harbor House

Dennis

Splash into Cape Cod charm at this poolside paradise with family-friendly waters and picnic baskets to go.

₹22,972 total

includes taxes & fees

18 Jun - 19 Jun

Seasonal outdoor pool, pool umbrellas, pool loungers

Holiday Hill Inn & Suites

Dennis Port

Sparkling family-friendly pool oasis awaits at this beach-convenient motel with mini golf fun.

₹13,860 total

includes taxes & fees

16 Jun - 17 Jun

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Choose what matters most at hotels with a pool in Osterville

Breakfast included

4 stars

Top Osterville Hotel Reviews

Iris Hotel Cape Cod

2/10 Terrible

"The room was pretty dirty, just from walking with my socks (brand new) by the end of one day were completely black, there was mold in the bathroom, toilet paper holder was broken off of the wall, first night there was not able to watch anything and relax until late at night because they didn’t have the credentials for the roku tv then when requesting a new room was able to “obtain them” aside from all of that was just the fact we asked for a roll away crib for our newborn and realized it was flipped upside down to see old pee stains over the mattress which I know babies are babies but you could at least replace the mattresses at a certain point and thought showed pretty low standards as a totality, needless to say they slept with us. Overall it was okay but the room was extremely unkept with “true cleaning” not a surface swipe and resell. aside from cleanliness everything else was okay."

Sea Crest Beach Resort

6/10 Okay

"When we first pulled up & registered we were very impressed - the lobby was nicely situated & the beach area was simply gorgeous. But . . . No one mentioned no elevators. Since my husband is disabled, we couldn’t take our beachfront room with balcony. he couldn’t do all those stairs. The staff put us in a room in the main building way back where the carpets are old & stained; the elevators dirty; & we had a partial ocean view - and much more of the roof. We were up most of the night listening to our neighbors having a very good time - walls are paper thin. My husband also slipped & fell in the shower / tub & we had to call 911 for assistance. The staff told him to “just use a towel for the bottom of the tub”. No mat or anti-slip grips in the shower & none offered. The building is poorly maintained with leaks evident on the ceilings. The restaurant was good - nice service, good food, very loud. Beautiful ocean view. This resort puts on a very good facade - when you pull up - Wow! But don’t be deceived by that! For the amount being charged per night, we expected more."

Frequently asked questions

What are some accommodation options with pools in Osterville?

Iris Hotel Cape Cod: Hotel located near Cape Cod Beaches. Features a snack bar/deli, an indoor pool and free self parking. Sea Crest Beach Resort: Hotel, 2-minute walk from Cape Cod Beaches. Offers a children's pool, a seasonal outdoor pool and a private beach. Bayside Resort Hotel: Hotel, 15-minute walk from Main Street Hyannis. Provides a seasonal outdoor pool, an indoor pool and 2 pool bars. Margaritaville Resort Cape Cod: Resort located near Cape Cod Beaches. Features a children's pool, an outdoor pool and a water park. AutoCamp Cape Cod: Hotel, 2-minute walk from Cape Cod Beaches. Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access.

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 Dowses Beach and 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.

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