The Best Hotels with a Pool in Osterville, MA from ￥16,716 in 2026

Q: What are some accommodations 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. Riviera Beach Resort : Hotel, 3-minute walk from Cape Cod Beaches. Offers a children's pool, a seasonal outdoor pool, and a private beach. 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. Margaritaville Resort Cape Cod : Resort located near Cape Cod Beaches. Features a children's pool, an outdoor pool, and a water park. Parker Beach Lodge : Hotel, 2-minute walk from Cape Cod Beaches. Offers 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

Ocean Street Inn on Hyannis Harbor

Hyannis

Seaside serenity awaits at this harbor-front motel, where nearby pools and marina access promise refreshing coastal relaxation.

￥22,066 total

includes taxes & fees

Jul 1 - Jul 2

Sandwich Lodge & Resort

Sandwich

Take a splash indoors or out at this dual-pool resort offering both year-round and seasonal aquatic escapes.

￥28,531 total

includes taxes & fees

Jul 8 - Jul 9

GuestLodge

West Dennis

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

￥16,716 total

includes taxes & fees

Jun 28 - Jun 29

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.

￥26,818 total

includes taxes & fees

Jul 1 - Jul 2

Sesuit Harbor House

Dennis

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

￥43,272 total

includes taxes & fees

Jun 29 - Jun 30

Seasonal outdoor pool, pool umbrellas, sun 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.

￥51,769 total

includes taxes & fees

Jul 8 - Jul 9

Seasonal outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas

Parker Beach Lodge

Bass River

Seasonal pool with loungers and umbrellas offers refreshing retreat near Hyannis Harbor at Cape Cod hotel.

￥34,678 total

includes taxes & fees

Jul 5 - Jul 6

Holiday Hill Inn & Suites

Dennis Port

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

￥31,321 total

includes taxes & fees

Jul 8 - Jul 9

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Choose what matters most at hotels with a pool in Osterville

Breakfast included

4 stars

Top Osterville Hotel Reviews

Riviera Beach Resort

8/10 Good

"Staff was friendly & helpful."

Sea Crest Beach Resort

10/10 Excellent

"Lovely property on the beach which was fantastic and why we choose to visit Staff was very courteous and professional. The toilet seats in our one bedroom suite were old and stained. They can easily be replaced. The light fixture in one bathroom was falling apart also an easy fix that won't cost much. I had a problem which was not the fault of anyone on the property. It was caused by a third party but, the manager listened to me respectfully, was empathetic, explained what happened and how to avoid it in the future. He waived our resort fees for our stay and offered us free breakfast. I was very impressed by him."

The Corsair & Cross Rip Oceanfront Resort

10/10 Excellent

"We loved our stay! We are new to the Cape and did not know that many of the beaches cost money to park and go to. Therefore, having direct beach access and chairs/umbrellas was amazing. I will mention they do not provide beach towels, however, which is important to know for planning. The food/drink options were also very convenient and Dennis Port is a great, central location."

Frequently asked questions

What are some accommodations 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. Riviera Beach Resort: Hotel, 3-minute walk from Cape Cod Beaches. Offers a children's pool, a seasonal outdoor pool, and a private beach. 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. Margaritaville Resort Cape Cod: Resort located near Cape Cod Beaches. Features a children's pool, an outdoor pool, and a water park. Parker Beach Lodge: Hotel, 2-minute walk from Cape Cod Beaches. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

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 Dowses Beach and 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.

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