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
Sep 11 - Sep 12
Tomorrow
Sep 12 - Sep 13
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Osterville hotels with a pool

An indoor swimming pool with clear blue water, white poolside chairs, and a mural of a coastal scene on the wall.
A small, single-story building with a porch and outdoor seating area.
A beach with a sandy shore and calm water.
A spacious kitchen with white cabinetry, a large window, and a view of the outdoors.

1. Craigville Beach Inn

Craigville Beach Inn
Centerville
  • Splash into beachside bliss with an indoor pool and complimentary beach shuttle service.
$111 nightly
$127 total
Oct 12 - Oct 13
Total with taxes and fees
Craigville Beach Inn
An indoor swimming pool with a lifeguard chair, a pool lift, and a wheelchair-accessible door.
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.

2. 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.
$134 nightly
$153 total
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Express Hyannis Cape Cod by IHG
An indoor swimming pool with clear water, surrounded by black chairs and tables.
A sunlit patio area with potted plants and a table with chairs.
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.

3. Hyannis Travel Inn

Hyannis Travel Inn
Hyannis
  • Splash into summer at this Cape Cod oasis with refreshing indoor and outdoor pools.
$108 nightly
$124 total
Sep 21 - Sep 22
Total with taxes and fees
Hyannis Travel Inn
An indoor swimming pool with a brick wall, a white table with chairs, and a large window.
A compact hotel room with a kitchenette, a bed, a dining area, and a view through a large window.
A multi-story hotel with a well-maintained lawn, outdoor seating area with chairs, and a wooden deck.
A Courtyard Resort sign, a building with a brick facade, and a parking lot.

4. Courtyard Resort

Courtyard Resort
Hyannis
  • Resort relaxation awaits with hot tub, indoor pool at Cape Cod getaway near Hyannis Harbor.
$100 nightly
$115 total
Oct 1 - Oct 2
Total with taxes and fees
Courtyard Resort
An indoor water park with a boat-shaped play area, a boat house, and a large slide.
A cozy lounge area with wicker furniture, a central round table, and a decorative archway with a sign.
A bar area with a high counter, multiple seating options, and a ceiling with a shark motif.
A hotel named 'Margaritaville Resort' with a prominent blue roof, large glass entrance, and outdoor seating area.

5. 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.
$199 nightly
$228 total
Oct 4 - Oct 5
Total with taxes and fees
Margaritaville Resort Cape Cod
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with windows.
A bathroom with a large mirror, a sink, and a shower area.
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.
A hotel room with two beds, a desk with a computer, a chair, and a window with curtains.

6. 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.
$151 nightly
$173 total
Oct 12 - Oct 13
Total with taxes and fees
Holiday Inn Hyannis by IHG
An indoor swimming pool with a blue ceiling and white poolside chairs.
A lobby with a wooden floor, a reception desk, a large window, and a ceiling fan.
A decorative shark sculpture with the text "Cape Sands Inn" at a beachside location.
A row of white buildings with balconies, outdoor seating, and flower beds.

7. Cape Sands Inn

Cape Sands Inn
West Yarmouth
  • Dive into year-round aquatic bliss with indoor and seasonal outdoor pools, complemented by a relaxing hot tub and sauna.
$84 nightly
$96 total
Sep 14 - Sep 15
Total with taxes and fees
Cape Sands Inn
An indoor swimming pool with clear blue water, tiled walls, and a ceiling painted in blue.
A long dining table with chairs, a kitchen area, and a large window.
A hotel room with a bed, a desk with a flat-screen TV, a coffee maker, a microwave, a vacuum cleaner, and a sliding door to a balcony.
A reception area with a check-in counter, blue chairs, a waiting area, and a glass door leading to a dining area.

8. Comfort Inn Hyannis - Cape Cod

Comfort Inn Hyannis - Cape Cod
Hyannis
  • Splash into relaxation with a serene indoor pool experience and bubbling hot tub retreat.
$106 nightly
$121 total
Oct 12 - Oct 13
Total with taxes and fees
Comfort Inn Hyannis - Cape Cod
A swimming pool with a tiled deck, lounge chairs, and a ceiling with recessed lighting.
A hotel room with two beds, a desk with a TV, a chair, and a large tapestry on the wall.
A modern hotel with a covered entrance, landscaped gardens, and a two-story structure.
A hotel reception desk with marble countertops, wooden paneling, and pendant lighting.

9. Aiden by Best Western Cape Cod - West Yarmouth

Aiden by Best Western Cape Cod - West Yarmouth
West Yarmouth
  • Swim in serenity at a beachside oasis with both indoor and seasonal outdoor pools.
$101 nightly
$116 total
Oct 12 - Oct 13
Total with taxes and fees
Aiden by Best Western Cape Cod - West Yarmouth
A swimming pool with clear blue water, surrounded by a tiled deck and a building with a green roof in the background.
A fire pit with chairs arranged around it, set on sandy ground with a wooden fence and foliage in the background.
A beach with clear skies and gentle waves.
A grassy area with blue Adirondack chairs arranged around a central fire pit. In the background, there are two buildings with a playground structure.

10. Sunbird Cape Cod Resort

Sunbird Cape Cod Resort
West Yarmouth
  • Splash into Cape Cod bliss with indoor and seasonal outdoor pools at this family-friendly resort.
$99 nightly
$113 total
Oct 1 - Oct 2
Total with taxes and fees
Sunbird Cape Cod Resort
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

Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"This quaint little hidden gem didn’t disappoint. We got exactly what was advertised. The gypsy theme was cute not too kitschy or overdone. The staff was friendly and quietly made sure everything was in its place and guests were comfortable. While we were there for a couples getaway there were quite a few families there to enjoy the last weekend of summer. Tbh I was a bit concerned as we were unloading the car, but between the 2 pools and the various outdoor areas we were able to enjoy a relaxing stay that wasn’t crowded by kids. We will definitely be back."
Najah 1-night trip
Posted 7 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Everything was good"
Rupinder 3-night trip
Posted 8 hours ago
Cape Sands Inn
Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"The staff from the front desk to the cafe were polite, helpful and very welcoming. Our room was truly handicap accessible, with a shower seat over the tub, adjustable shower and amenities within easy reach. Breakfast was beyond expectations. We stayed here before and after our excursion to MV and we would highly recommend to anyone traveling in Cape Cod or going to Martha’s Vineyard or Nantucket."
Howie 1-night trip
Posted 10 hours ago
Iris Hotel Cape Cod
Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"This was amazing! From the moment we walked in the lobby we felt so welcome! We booked a king room with a pullout couch for the 5 of us, 2 adults and 3 kids and the woman at the front desk asked if we would prefer 2 queen beds instead bc there was more room for the 5 of us to sleep on. We accepted and we were so grateful. The beds were so comfortable. The people are so polite, beautiful room, AMAZING location! We spent a little more than we wanted on this trip for the room but it was worth it 10000%. My daughter fell and got hurt and an employee asked was asking if she was ok. She said if you need anything please let us know. We walked back to our room and sat my daughter down and decided to call and ask the front desk if they had ice packs and someone brought ice to our room, bandaids and water bottles, and asked if we needed anything else. Staff was amazing! I felt safe here. The only thing I didnt like was that there were so many stairs. There were different levels. That was the only negative thing I have to say about this place! Will definitely be coming back!!!"
Sean 2-night trip
Posted 16 hours ago
Hyannis Harbor Hotel
Sunbird ANNEX Resort

Sunbird ANNEX Resort

8/10 Good
"Very clean, well appointed motel. Staff friendly and accommodating. Breakfast was fresh and delicious. A very good value for Cape Cod."
Paul 1-night trip
Posted 1 day ago
Sunbird ANNEX Resort
Faraway Martha's Vineyard

Faraway Martha's Vineyard

10/10 Excellent
"The Faraway hotel in Edgartown is one of the nicest hotels on Martha's Vineyard. The location is unbeatable. They have their own parking lot which is key on the island. From the time you walk into the stunning lobby you are met by attentive staff and the hotels own signature fragrance. The rooms are spacious, updated and very clean. And the pool is an oasis in itself. I wouldn't stay anywhere else on the island."
Pamela 1-night trip
Posted 3 days ago
Faraway Martha's Vineyard

Frequently asked questions

What are some accommodations with pools in Osterville?
Margaritaville Resort Cape Cod: Resort located near Cape Cod Beaches. Features a children's pool, an indoor pool, and a water park. Bayside Resort Hotel: Hotel located near Cape Cod Beaches. Offers a seasonal outdoor pool, an indoor pool, and 2 pool bars. 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. Holiday Inn Express Hyannis Cape Cod by IHG: Hotel located near Hyannis Harbor. Features a children's pool, an indoor pool, and a sauna. Cape Sands Inn: Offers a seasonal outdoor pool, an indoor pool, and a sauna.
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