The Best Hotels with a Pool in Osterville, MA from AED 592 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.

AED 462 total

includes taxes & fees

1 Jul - 2 Jul

Sandwich Lodge & Resort

Sandwich

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

AED 592 total

includes taxes & fees

1 Jul - 2 Jul

GuestLodge

West Dennis

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

AED 331 total

includes taxes & fees

30 Jun - 1 Jul

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.

AED 645 total

includes taxes & fees

6 Jul - 7 Jul

Sesuit Harbor House

Dennis

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

AED 1,157 total

includes taxes & fees

30 Jun - 1 Jul

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.

AED 1,004 total

includes taxes & fees

30 Jun - 1 Jul

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.

AED 838 total

includes taxes & fees

5 Jul - 6 Jul

Holiday Hill Inn & Suites

Dennis Port

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

AED 708 total

includes taxes & fees

6 Jul - 7 Jul

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Choose what matters most at hotels with a pool in Osterville

Breakfast included

4 stars

Top Osterville Hotel Reviews

The Corsair & Cross Rip Oceanfront Resort

8/10 Good

"A nicely kept beachfront hotel. Had a room with view of the ocean which was very calming."

Holiday Hill Inn & Suites

8/10 Good

"Well run and clean and just what we needed for a one night stay to attend a wedding near by. There was a funny smell in the room (perhaps a perfumed cleaning product?) and you needed to be careful going down the outside stairs at the end of the property (we stayed on the second floor) because the last step was not the same as the others. It is an older property, but perfectly adequate for the price. The person who checked us in was very helpful, efficient and knowledgable."

Sea Crest Beach Resort

10/10 Excellent

"Was looking for pet friendly on the beach for a long weekend on the Cape. I hadn’t been to SeaCrest in over a decade. Property was in great shape and looked like it was recently renovated. Fireplace studio was great with a view of Old Silver Beach. Beach service was quick and efficient. There were several events on the property and noise was never an issue. Meals were great. I wish the pizza place was open!"

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Osterville Hotels by Star Rating

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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