A house by a lake with boats.

Find Hotels with a Pool in Osterville, MA

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Osterville Hotels with a Pool

Tonight
Oct 9 - Oct 10
Tomorrow
Oct 10 - Oct 11
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Osterville hotels with a pool

An indoor swimming pool with lounge chairs and tables, a tiled wall, and a ceiling with recessed lighting.
A hotel room with two beds, a desk, a chair, and a window with a view of trees.
A coffee station with two coffee machines, a coffee press, and various coffee pods and cups.
A buffet area with a display of sweet rolls, a sign indicating the roll selection process, and a patterned wall in the background.

1. Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG
Hyannis
  • Splash into an aquatic escape at this Cape Cod hotel featuring both an indoor pool and dedicated children's pool for all-ages fun.
$101 nightly
$116 total
Oct 29 - Oct 30
Total with taxes and fees
Holiday Inn Express Hyannis Cape Cod by IHG
An indoor swimming pool with clear blue water, white poolside chairs, and a mural of a coastal scene on the wall.
A beach with a sandy shore and calm water.
A compact kitchen with white cabinets, a microwave, and a sink. There is a small rug on the floor and a bed with a floral bedspread in the adjacent room.
A spacious kitchen with white cabinetry, a large window, and a view of the outdoors.

2. Craigville Beach Inn

Craigville Beach Inn
Centerville
  • Splash into beachside bliss with an indoor pool and complimentary beach shuttle service.
$148 nightly
$170 total
Oct 12 - Oct 13
Total with taxes and fees
Craigville Beach Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with windows.
A gym with various cardio and strength training equipment, including treadmills, elliptical machines, and weight machines.
A hotel room with two beds, a desk with a computer, a chair, and a window with curtains.
A hotel room with a gray sofa, a television on a stand, a sliding door, a framed picture on the wall, and a lamp on a side table.

3. Holiday Inn Hyannis by IHG

Holiday Inn Hyannis by IHG
Hyannis
  • Splash into poolside perfection with dual swimming options and a steamy hot tub escape.
$127 nightly
$145 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Hyannis by IHG
An indoor swimming pool with a tiled edge, a diving board, and multiple chairs around the pool.
A reception area with a wooden reception desk, a digital kiosk, and a fireplace.
A modern conference room with a long table, chairs, a flat-screen TV, and pendant lighting.
A Fairfield by Marriott hotel with a large sign, a covered entrance, and a building with a tower.

4. Fairfield Inn & Suites by Marriott Cape Cod Hyannis

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.
$127 nightly
$145 total
Oct 26 - Oct 27
Total with taxes and fees
Fairfield Inn & Suites by Marriott Cape Cod Hyannis
An indoor swimming pool with clear water, surrounded by black chairs and tables.
A hotel room with two beds, a desk, a chair, a lamp, and a nightstand with a phone and a small table.
A man sitting at a table with a laptop, overlooking a pool area with chairs and tables.
A sunlit patio area with potted plants and a table with chairs.

5. Hyannis Travel Inn

Hyannis Travel Inn
Hyannis
  • Splash into summer at this Cape Cod oasis with refreshing indoor and outdoor pools.
$99 nightly
$113 total
Oct 12 - Oct 13
Total with taxes and fees
Hyannis Travel Inn
An indoor swimming pool with a high ceiling and large windows.
View from property
A modern bar area with a curved wooden counter, multiple stools, and a display case with beverages.
A hotel reception area with a digital display showing today's weather and this week's forecast.

6. Courtyard By Marriott Cape Cod Hyannis

Courtyard By Marriott Cape Cod Hyannis
Hyannis
  • Swim year-round at this spotless indoor pool hotel, steps from Hyannis Harbor.
$126 nightly
$144 total
Oct 25 - Oct 26
Total with taxes and fees
Courtyard By Marriott Cape Cod Hyannis
A resort pool area with multiple lounge chairs and umbrellas, a hot tub, and a large building in the background.
A modern living room with two sofas, a coffee table, and a stone wall with a fireplace.
An outdoor seating area with wicker furniture, umbrellas, and a stone wall.
A two-story hotel with a curved facade, a balcony, and a sign indicating a vacancy.

7. Hyannis Harbor Hotel

Hyannis Harbor Hotel
Hyannis
  • Splash into seaside fun with three distinct pools and a poolside bar steps away from Hyannis Harbor.
$122 nightly
$140 total
Oct 21 - Oct 22
Total with taxes and fees
Hyannis Harbor Hotel
An indoor water park with a boat-shaped play area, a boat house, and a large slide.
A bar area with a high counter, multiple seating options, and a ceiling with a shark motif.
A spacious lobby with a large blue mural, comfortable seating areas, and a prominent circular floor design.
A hotel named 'Margaritaville Resort' with a prominent blue roof, large glass entrance, and outdoor seating area.

8. Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod
Hyannis
  • Poolside paradise at this Cape Cod resort with outdoor pools, waterpark, and a lazy river waiting for you.
$193 nightly
$221 total
Oct 25 - Oct 26
Total with taxes and fees
Margaritaville Resort Cape Cod
An indoor swimming pool with a brick wall, a white table with chairs, and a large window.
A multi-story hotel with a well-maintained lawn, outdoor seating area with chairs, and a wooden deck.
A compact hotel room with a kitchenette, a bed, a dining area, and a view through a large window.
A Courtyard Resort sign, a building with a brick facade, and a parking lot.

9. Courtyard Resort

Courtyard Resort
Hyannis
  • Resort relaxation awaits with hot tub, indoor pool at Cape Cod getaway near Hyannis Harbor.
$113 nightly
$130 total
Oct 13 - Oct 14
Total with taxes and fees
Courtyard Resort
A large indoor swimming pool with multiple lanes, surrounded by rows of chairs and a high ceiling with large windows.
An outdoor patio with round tables and chairs, a fire pit, and a covered seating area with string lights.
A DoubleTree hotel with a brick facade and a large sign.
A modern lounge area with a stone wall, a flat-screen TV, and comfortable seating.

10. Doubletree by Hilton Cape Cod - Hyannis

Doubletree by Hilton Cape Cod - Hyannis
Hyannis
  • Refreshing retreat featuring both indoor and heated outdoor pools for year-round aquatic enjoyment with poolside lounging options.
$125 nightly
$143 total
Nov 8 - Nov 9
Total with taxes and fees
Doubletree by Hilton Cape Cod - Hyannis
View all properties

Choose what matters most at hotels with a pool in Osterville

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Osterville Hotel Reviews

Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"Good location"
Mary 1-night trip
Posted 1 day ago
Iris Hotel Cape Cod
Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Location was fantastic! It’s centrally located and walking distance to many restaurants and taverns in Hyannis. Everyone at the front desk was friendly. Room was spacious. Breakfast was adequate."
Crystal 1-night trip
Posted 1 day ago
Hyannis Travel Inn
Holiday Inn Express Hyannis Cape Cod by IHG

Holiday Inn Express Hyannis Cape Cod by IHG

8/10 Good
"Hotel was great, room was tiny, but clean and beds were comfortable. Breakfast was good."
Cheri 2-night trip
Posted 1 day ago
Holiday Inn Express Hyannis Cape Cod by IHG
Sea Crest Beach Resort

Sea Crest Beach Resort

10/10 Excellent
"We loved our stay at the Sea Crest. The woman at the front desk was enormously helpful and kind during our stay, making sure we had everything we needed. Gorgeous view from the room, beautiful beach. If only it was warm enough to swim in the ocean, it would have been perfect."
Deborah 1-night trip
Posted 1 day ago
Sea Crest Beach Resort
Hyannis Plaza Hotel

Hyannis Plaza Hotel

10/10 Excellent
"Very happy"
Sharon 1-night trip
Posted 2 days ago
Hyannis Plaza Hotel

Frequently asked questions

What are some accommodations with pools in Osterville?
Sea Crest Beach Resort: Hotel, 2-minute walk from Cape Cod Beaches. Features a children's pool, a seasonal outdoor pool, and a private beach. Iris Hotel Cape Cod: Offers a snack bar/deli, an indoor pool, and free self parking. Margaritaville Resort Cape Cod: Resort located near Hyannis Harbor. Provides a children's pool, an indoor pool, and a water park. Lighthouse Inn: Hotel, 4-minute walk from Cape Cod Beaches. Features a private beach, a seasonal outdoor pool, and a snack bar/deli. Bayside Resort Hotel: Hotel located near Hyannis Harbor. Offers a seasonal outdoor pool, an indoor pool, and 2 pool bars.
What is there to see and do in Osterville?
Surround yourself with nature at Cape Cod Beaches and Dowses Beach. Discover sights such as Stand Up & Paddle Cape Cod and Public Beach during your stay.
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