A wooden pier leading to a marina with boats docked.

Chebeague Island Hotel with Pool

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chebeague Island Hotel with Pool

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Chebeague Island hotels with a pool

An indoor swimming pool with a clear water surface, surrounded by beige tiled walls and a blue accent wall.
A reception area with a modern design, featuring a seating area with yellow chairs, a reception desk, and a large wall mural.
A Holiday Inn Express building with a covered entrance, multiple floors, and a clear sky.
A modern dining area with round tables and chairs, a coffee station, and a view of the city.

1. Holiday Inn Express Hotel & Suites Freeport by IHG

Holiday Inn Express Hotel & Suites Freeport by IHG
Freeport
  • Serene indoor pool sanctuary in Freeport awaits with extended hours for swimming and relaxation near popular attractions.
HK$745
HK$813 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Hotel & Suites Freeport by IHG
A swimming pool with clear blue water, surrounded by large windows offering views of trees and a clear sky.
A hotel lobby with a seating area, a snack bar, and a refrigerator.
A spacious lobby with a blue wall, a reception desk, a large mirror, and seating areas with a patterned table and chairs.
An outdoor patio with a row of tables and chairs, a green umbrella, and a wooden fence.

2. Hampton Inn Freeport/Brunswick

Hampton Inn Freeport/Brunswick
Freeport
  • Dip into year-round pool fun at this hotel with a sparkling indoor swimming sanctuary.
HK$766
HK$835 total
includes taxes & fees
28 Oct - 29 Oct
Hampton Inn Freeport/Brunswick
A swimming pool with a tiled deck, lounge chairs, and a ceiling with recessed lighting.
An outdoor patio area with wicker furniture, string lights, and a barbecue grill.
A hotel room with a bed, a TV, a nightstand, a window with a view of the water, and a wooden headboard.
A brick building with a large entrance and a sign that reads "Residence Inn Marriott".

3. Residence Inn by Marriott Portland Downtown/Waterfront

Residence Inn by Marriott Portland Downtown/Waterfront
Downtown Portland
  • Plunge into relaxing aquatic serenity at this Portland hotel's pristine indoor pool, just minutes from waterfront attractions.
HK$863
HK$955 total
includes taxes & fees
16 Nov - 17 Nov
Residence Inn by Marriott Portland Downtown/Waterfront
An indoor swimming pool with clear glass walls, blue cushioned chairs, and a tiled floor.
A building with a sign reading "L.L.Bean" and a rock waterfall feature in front.
Restaurant
A Hilton Garden Inn with a well-lit entrance, a signboard, and a parking area.

4. Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown
Freeport
  • Dive into a refreshing aquatic escape at this Freeport hotel with an inviting indoor pool.
HK$798
HK$870 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Freeport Downtown
An indoor swimming pool with clear signage, including pool user capacity and no diving rules.
A hotel room with a sofa, a bed, a wall-mounted artwork, and a lamp.
A modern hotel lobby with a central bar area, multiple seating arrangements, and large windows providing views of the outside.
Lobby lounge

5. SpringHill Suites by Marriott Freeport Brunswick

SpringHill Suites by Marriott Freeport Brunswick
Freeport
  • Plunge into relaxation at the indoor pool, where comfort meets convenience in this modern Freeport hotel near shopping gems.
HK$720
HK$785 total
includes taxes & fees
16 Nov - 17 Nov
SpringHill Suites by Marriott Freeport Brunswick
A swimming pool with lounge chairs and tables, surrounded by a well-lit indoor area with a view of the outside.
A Holiday Inn hotel with a modern design, featuring a large entrance canopy and multiple floors.
A modern bar area with a long counter, multiple seating options, and a built-in fire feature.
A conference room with a stage featuring a large screen displaying the word 'Float' and a banner for the University of Maine.

6. Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG
Downtown Portland
  • Sleek indoor pool with loungers awaits in this scenic Portland hotel with a sauna retreat.
HK$793
HK$881 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Portland-By the Bay by IHG
An indoor swimming pool with lounge chairs and a view of the outdoors.
A dining area with a fireplace, a green sofa, and a table set with food and flowers.
A two-story building with a large glass conservatory and yellow umbrellas in the garden area.
A bathroom with a shower, a bathtub, and a sink.

7. The Harraseeket Inn & Event House Freeport Downtown

The Harraseeket Inn & Event House Freeport Downtown
Freeport
  • Serene indoor pool and cosy fireside relaxation offer year-round bliss at this Freeport retreat.
HK$1,012
HK$1,103 total
includes taxes & fees
8 Nov - 9 Nov
The Harraseeket Inn & Event House Freeport Downtown
A modern living room with dark blue walls, large windows, and a view of a landscaped garden.
A bathroom with a shower, a sink with a mirror, and a towel rack.
A hotel room with two beds, a desk, and a view of the outdoors.
A living room with two armchairs, a coffee table, and a TV. There is a door leading outside, a window with a view, and a patterned wall.

8. Best Western Freeport Inn

Best Western Freeport Inn
Freeport
  • Sun-soaked summer splashing awaits at this peaceful inn with a seasonal outdoor pool.
HK$761
HK$830 total
includes taxes & fees
1 Nov - 2 Nov
Best Western Freeport Inn
A swimming pool with clear blue water, surrounded by lounge chairs and a brick wall.
A brick building with a sign reading "WAYPOINT" and outdoor seating with tables, chairs, and a fire pit.
A spacious lobby with multiple seating areas, a fireplace, and large windows.
A chef in a black uniform and white hat, holding a ladle and a bowl, with various dishes in front of him.

9. Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine
Portland
  • Splash into serenity at this indoor pool sanctuary with luxurious loungers and post-swim relaxation.
HK$933
HK$1,032 total
includes taxes & fees
15 Nov - 16 Nov
Embassy Suites by Hilton Portland Maine
An indoor swimming pool with clear water, a diving board, and a lifeguard chair.
The exterior of a Courtyard by Marriott hotel with a glass entrance, outdoor seating area, and a stone facade.
A modern hotel lobby with a reception desk, a seating area, and a large wall mural.
A hotel room with a large bed, a desk with a computer, a TV, and a view of the city and water.

10. Courtyard Portland Downtown/Waterfront

Courtyard Portland Downtown/Waterfront
Downtown Portland
  • Splash into aquatic luxury with a year-round indoor pool oasis at this city centre Portland hotel.
HK$810
HK$896 total
includes taxes & fees
16 Nov - 17 Nov
Courtyard Portland Downtown/Waterfront
View all properties

Choose what matters most at hotels with a pool in Chebeague Island

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chebeague Island Hotel Reviews

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"Just what my family needed for a couple days while we ate lobster rolls from all the restaurants we could. Conveniently located close enough but far enough. Safe area, quiet location, pretty decent breakfast sandwiches and other snacks in the am before we took off to explore for the day. Would def recommend and stay again."
Mercedes 2-night trip
Posted 1 hour ago
Fireside Inn & Suites Portland
Grand Beach Inn

Grand Beach Inn

8/10 Good
"Good stay"
Edward 4-night trip
Posted 2 hours ago
Grand Beach Inn
Clarion Pointe South Portland

Clarion Pointe South Portland

10/10 Excellent
"Great room. Comfortable beds. Cleaning could have been a little better but all in all a very nice hotel. Very friendly staff, and very helpful. I would return again if I need a hotel."
Paul Allen 4-night trip
Posted 4 hours ago
Clarion Pointe South Portland
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

8/10 Good
"The location was perfect to walk around and explore the port. Easily discover restaurants,shops, and directly across from art museum. Room had a nice bay view (extra for bay) surfaces were clean but need a more thorough cleaning as we found items under the couch. Food options are available but with so many restaurants only steps away I would venture out from the hotel. Breakfast was standard buffet,did not have their dinner (available at buffet location). Pool and amenities seemed underutilized and neglected as pool was freezing (stated that pool was 86 but felt like 64), a bit dirt need to be removed and saunas took a long time to heat up. Not terrible just kinda of there. Gym looked ok. Staff was a bit of a mix bag, First Lady was helpful but blunt( we were early so I get it), second who check us in had computer issues not her fault but she forgot to give us food vouchers lucky later we asked and received , third gave us food vouchers and was very very kind and helpful. If you visit make sure you’re not early, tell them you have the breakfast, and if the pool is cold tell someone. Easy access to parking garage but pricey (should be included with stay… hey who said that) recommend for travelers with no car as old port is near and area is walkable."
Marissa 2-night trip
Posted 10 hours ago
Holiday Inn Portland-By the Bay by IHG
Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"Staff was very helpful & friendly"
Mike 1-night trip
Posted 20 hours ago
Hampton Inn Portland Downtown - Waterfront
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

8/10 Good
"Extremely well located in Portland, in the heart of the old town and central to everything. I'm glad we chose this hotel rather than others that were mostly newer. The breakfast and bar options were good."
shaun 2-night trip
Posted 1 day ago
Portland Regency Hotel & Spa

Frequently asked questions

What are some accommodation options with pools in Chebeague Island?
Quality Inn & Suites South Portland: Hotel located near State Theatre. Provides free self parking, a pool and complimentary wireless Internet access. Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel: Hotel located near Maine Mall. Features an indoor pool, an outdoor pool and daily. Clarion Hotel Portland Airport ME: Features a seasonal outdoor pool, an indoor pool and a sauna. Clarion Pointe South Portland: Hotel, 4-minute walk from Cross Insurance Arena. Provides a sauna, a pool and complimentary bicycles. Portland Harbor Hotel: Hotel located near State Theatre. Features buffet, a seasonal outdoor pool and complimentary wireless Internet access.
What is there to see and do in Chebeague Island?
Make a point to visit attractions such as Portland Observatory and Maine Narrow Gauge Railroad. Discover sights such as Little John Island Preserve, Wolfe's Neck Woods State Park and Bailey Island Bridge during your stay.
When is the best time to book a hotel with a pool in Chebeague Island?
Taking the local weather in Chebeague Island into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chebeague Island are January, March, February and December, with each month seeing an average of 19 cm of snowfall.

Explore a world of travel with Expedia