Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Find vacation rentals that suit your style
Cabins
Aparthotels
Apartments
Villas
Condos
Cottages
Chalets
Our top choices for Chebeague Island villas
1. Westwind on Winter St - 2 bedroom townhouse apartment near downtown Topsham/Brunswick
Westwind on Winter St - 2 bedroom townhouse apartment near downtown Topsham/BrunswickTopsham
8.0 out of 10, Very good, (2 reviews)
8.0/10
Very good
(2 reviews)
"Convenient location. Easy check in and communication with hosts. Worked well for our family of 4."
"Convenient location. Easy check in and communication with hosts. Worked well for our family of 4."
Natalie S.
$242 nightly
The price is $242
$242 total
Dec 1 - Dec 2
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Learn more about Chebeague Island
Rent bikes to explore this peaceful island's rocky beaches and historic 1920s inn, where fresh lobster awaits. Take the passenger ferry from Cousins Island for a day trip, then kayak along the quiet coastline or hike wooded trails.
Top reviews in Chebeague Island
Hampton Inn Freeport/Brunswick
Hampton Inn Freeport/BrunswickFreeport
10/10 Excellent
The staff were excellent as was the accommodations such as the indoor heated pool and the breakfast. My wife and I were above all, very blessed to be able to have our "puppy-dog," with us!
The staff were excellent as was the accommodations such as the indoor heated pool and the breakfast. My wife and I were above all, very blessed to be able to have our "puppy-dog," with us!
Dwight
SpringHill Suites by Marriott Freeport Brunswick
SpringHill Suites by Marriott Freeport BrunswickFreeport
10/10 Excellent
Great hotel!
Great hotel!
Paige
Hilton Garden Inn Freeport Downtown
Hilton Garden Inn Freeport DowntownFreeport
10/10 Excellent
Very nice hotel
Very nice hotel
Michael
The Harraseeket Inn & Event House Freeport Downtown
The Harraseeket Inn & Event House Freeport DowntownFreeport
10/10 Excellent
Going to the Harraseeket Inn is like time traveling, but with the option of taking a smart phone and having the electricity to charge it. It's like that movie, "Somewhere in Time," like you've walked through a time portal by the power of hypnotic suggestion and an Expedia booking. But it is very much, at the same time, part of the present. They have a pool, and the restaurant is quintessentially the definition of a timeless Maine eatery. The afternoon tea is pleasant and steeped with charm. The...
Going to the Harraseeket Inn is like time traveling, but with the option of taking a smart phone and having the electricity to charge it. It's like that movie, "Somewhere in Time," like you've walked through a time portal by the power of hypnotic suggestion and an Expedia booking. But it is very much, at the same time, part of the present. They have a pool, and the restaurant is quintessentially the definition of a timeless Maine eatery. The afternoon tea is pleasant and steeped with charm. The...
Bruno
Inn On Peaks Island
Inn On Peaks IslandPeaks Island
10/10 Excellent
Beautiful spot right next to the ferry drop off. Views of the ocean, outdoor dining, and lovely rooms.
Beautiful spot right next to the ferry drop off. Views of the ocean, outdoor dining, and lovely rooms.
Devon
Cambria Hotel Portland Downtown-Old Port
Cambria Hotel Portland Downtown-Old PortDowntown Portland
10/10 Excellent
very friendly staff. Room was clean, comfortable and big.
Valet was expensive ($40/night)
I think the valet may have caused a small dent in the drive car door (brand new car, 5 miles on it)
very friendly staff. Room was clean, comfortable and big.
Valet was expensive ($40/night)
I think the valet may have caused a small dent in the drive car door (brand new car, 5 miles on it)
seth
Hilton Garden Inn Portland Downtown Waterfront
Hilton Garden Inn Portland Downtown WaterfrontDowntown Portland
10/10 Excellent
This hotel is in the perfect location to walk to everything around the waterfront. I had a really late check in because of a delayed flight and the staff was very accommodating. I would definitely recommend this hotel to anyone visiting Portland!
This hotel is in the perfect location to walk to everything around the waterfront. I had a really late check in because of a delayed flight and the staff was very accommodating. I would definitely recommend this hotel to anyone visiting Portland!
Robert
Residence Inn by Marriott Portland Downtown/Waterfront
Residence Inn by Marriott Portland Downtown/WaterfrontDowntown Portland
10/10 Excellent
Great location. Easy access for day trips up the coast, Boston etc. Boys loved the pool. Staff was responsive and took care of minor requests timely. Breakfast crew was outstanding and really made us feel appreciated for staying on property.
Great location. Easy access for day trips up the coast, Boston etc. Boys loved the pool. Staff was responsive and took care of minor requests timely. Breakfast crew was outstanding and really made us feel appreciated for staying on property.
Mark
AC Hotel Portland Downtown/Waterfront, ME
AC Hotel Portland Downtown/Waterfront, MEDowntown Portland
10/10 Excellent
I'd stay again nice and quiet friendly staff shuttle service was on point.
I'd stay again nice and quiet friendly staff shuttle service was on point.
Craig
Candlebay Inn
Candlebay InnFreeport
10/10 Excellent
Very cute B and B. Nice personal touches, snacks and extra amenities, toys for your pet, wonderful breakfast. Connie was very personable and knew alot about surrounding area. Within walking of lots of shops and restaurants. Perfect spot. Clean, would stay again.
Very cute B and B. Nice personal touches, snacks and extra amenities, toys for your pet, wonderful breakfast. Connie was very personable and knew alot about surrounding area. Within walking of lots of shops and restaurants. Perfect spot. Clean, would stay again.
Sheree Lee
Embassy Suites by Hilton Portland Maine
Embassy Suites by Hilton Portland MainePortland
10/10 Excellent
I don’t have any complaints….breakfast was the best I’ve had.
I don’t have any complaints….breakfast was the best I’ve had.
Michael
Courtyard Portland Downtown/Waterfront
Courtyard Portland Downtown/WaterfrontDowntown Portland
10/10 Excellent
I changed my hotel to this one since it listed a EV car charger. Apparently the city owns the charger and it is damaged. BUT I was pleasantly surprised by how nice everything else was at the hotel.
I changed my hotel to this one since it listed a EV car charger. Apparently the city owns the charger and it is damaged. BUT I was pleasantly surprised by how nice everything else was at the hotel.
Anonymous traveler
Aloft by Marriott Portland Downtown Waterfront ME
Aloft by Marriott Portland Downtown Waterfront MEDowntown Portland
10/10 Excellent
great
great
Lindsay
The Freeport Hotel, an Ascend Collection Hotel
The Freeport Hotel, an Ascend Collection HotelFreeport
10/10 Excellent
Despite friendly and cooperative staff there is much more that needs to be done as far as making sure there is clean linen and amenities that are readily available.
Despite friendly and cooperative staff there is much more that needs to be done as far as making sure there is clean linen and amenities that are readily available.
Mark
Best Western Freeport Inn
Best Western Freeport InnFreeport
10/10 Excellent
Clean and great beds!
Clean and great beds!
Donna
The Nicholson Inn
The Nicholson InnFreeport
10/10 Excellent
It was just a great place to stay. Very quaint, the Inn keepers were very friendly and helpful with what to do in the surrounding areas. Lots of outlet namebrand outlet stores and of course the new LL Bean Flagship store. Which was amazing. Would definitely stay again
It was just a great place to stay. Very quaint, the Inn keepers were very friendly and helpful with what to do in the surrounding areas. Lots of outlet namebrand outlet stores and of course the new LL Bean Flagship store. Which was amazing. Would definitely stay again
David