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Check prices for these dates

Next weekend
7 Mar - 9 Mar
In two weeks
14 Mar - 16 Mar
In one month
28 Mar - 30 Mar
In two months
25 Apr - 27 Apr

Compare 456 Vacation Homes in Chebeague Island with updated reviews, rates, and availability.

Oceanfront Cabin-Castle in Maine Woods
Interior

Oceanfront Cabin-Castle in Maine Woods

9.8 out of 10, Exceptional, (13)
"This cabin is something incredibly singular and special. It is imbued with the legacy of the Hall family, and you can read their history as you explore the house. The view is unbelievable - waking up, going downstairs, and being that close to the ocean is so peaceful. We could have spent a month reading as nearly every room is a library. The kitchen is stocked with some great old cast irons and lobster pots for whatever one would need. The China and dining wear even had character and...
Oceanfront Cabin-Castle in Maine Woods
Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator
Outdoor dining

Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator

9.6 out of 10, Exceptional, (55)
"Beautiful house with lots of space. Comfortable and easy check in. Great area too"
The price is AED 2,200
AED 4,548 total
includes taxes & fees
2 Mar - 3 Mar
Sensational Beachfront Property Old Orchard Beach, Maine, with indoor elevator
The Perfect Beach Escape: Cozy 4-Bedroom Retreat
On the beach, sun loungers, beach towels

The Perfect Beach Escape: Cozy 4-Bedroom Retreat

10.0 out of 10, Exceptional, (95)
"We traveled to Old Orchard during February break. While OOB didn’t have a lot going on we were able to travel around Maine with an oceanfront home base. The beach was nearly empty for daily walks, plenty of sunshine to bundle up and sit on the upper deck in, and a lot of snow! We did enjoy a nor’easter while we were there. The driveway was cleared the next day and the front stairs were cleaned. We did have to do the deck out back to enjoy it. The house has everything you could need for a rental....
The Perfect Beach Escape: Cozy 4-Bedroom Retreat
Charming 110-year former Inn 10' from the Ocean!
Property grounds

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (116)
"Stunning location. Dog friendly beach. Lighthouse in walking distance. "
Charming 110-year former Inn 10' from the Ocean!
Five miles from the beach, newly remodeled home with lots of privacy.
Fridge, microwave, oven, stovetop

Five miles from the beach, newly remodeled home with lots of privacy.

10.0 out of 10, Exceptional, (48)
"This is a lovely place for us to stay, it is always clean and the owners are really wonderful. It is the place for us to stay while visiting"
Five miles from the beach, newly remodeled home with lots of privacy.
The Globe House on Munjoy Hill - Walk to Breweries
Fridge, microwave, oven, stovetop

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries
East Grand Ave Fabulous Cottage
Beach

East Grand Ave Fabulous Cottage

9.2 out of 10, Wonderful, (131)
"The picture on VRBO leads you to believe you just go down the pathway shown to get to the beach when you are actually in a neighborhood and have to walk down the street to get to the beach. The house was very clean and both beds were very comfortable. The host was very fast to respond to my messages. Needs clean shower liner. We enjoyed our stay. "
East Grand Ave Fabulous Cottage
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Fridge, microwave, oven, stovetop

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Orchid Harbor, Bailey Island 3BR
Miscellaneous

Orchid Harbor, Bailey Island 3BR

"We enjoyed our weekend tremendously, especially being right on the beach, with miles of private access to the rocky shores to search for treasures and sea glass! Thank you so much!"
Orchid Harbor, Bailey Island 3BR
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Exterior

Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

9.8 out of 10, Exceptional, (68)
"Great house very comfortable and well appointed. Very roomy for our entire family. Nice to have en suite bathrooms with all the bedrooms. The host was very good with communication. Located on a busy road and the driveway is on a curve which made it a little challenging entering and exiting the property. "
Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
TV

Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay. The house was clean and the jacuzzi was much enjoyed. We let our vacation happy!"
Private 3BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi
Beautiful, Spacious Home, minutes to the Old Port!
Property grounds

Beautiful, Spacious Home, minutes to the Old Port!

10.0 out of 10, Exceptional, (1)
"We stayed for night with couples and friends. We had an amazing time and the place was so clean and exactly as described. "
The price is AED 455
AED 1,361 total
includes taxes & fees
9 Mar - 10 Mar
Beautiful, Spacious Home, minutes to the Old Port!
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
Interior

Charming ocean-view cottage just 10 minutes from downtown Freeport shops

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a fantastic stay with our family (including our 3yo). The home was exactly as described/photos show, and the view is simply amazing. Everything worked as expected, and the kids toys were an added bonus. Great communication with the host, would happily stay here again!"
Charming ocean-view cottage just 10 minutes from downtown Freeport shops
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
TV, fireplace, video games, DVD player

Bayfront home with 270-degree views, large deck & porch - near Popham Beach

8.2 out of 10, Very Good, (29)
"The house is beautiful, comfortable and was pristine when we checked in. Decks and screened porch are wonderful. The kids loved the 3rd floor bedroom space, and it was fabulous being so close to Popham Beach. Definitely recommend. Kitchen on 2nd floor ... so have some strong helpers to bring in groceries ;)"
Bayfront home with 270-degree views, large deck & porch - near Popham Beach
Breathtaking 35 Acre Private Oceanfront Compound with countless amenities!
Dining

Breathtaking 35 Acre Private Oceanfront Compound with countless amenities!

10.0 out of 10, Exceptional, (2)
"House was perfect for our family vacation and you could not ask for better hosts. We look forward to returning soon."
Breathtaking 35 Acre Private Oceanfront Compound with countless amenities!
Ocean Views! Walk to the Beach!
Smart TV

Ocean Views! Walk to the Beach!

9.8 out of 10, Exceptional, (13)
"Nice and clean, big and comfortable. Everything you’d need for a group. plenty of towels and a back yard to roast marshmallows. Perfect location with access to beach and the pier!!! "
Ocean Views! Walk to the Beach!
Coastal Gathering House - Spacious 4-bedroom house close to Portland
Interior

Coastal Gathering House - Spacious 4-bedroom house close to Portland

Coastal Gathering House - Spacious 4-bedroom house close to Portland
Edgewater Retreat on Little Sebago Lake - Lakefront w/Sauna & EV Charger
Sun loungers, beach towels

Edgewater Retreat on Little Sebago Lake - Lakefront w/Sauna & EV Charger

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay in Gray. Thank you for helping us. Most of us were out kayaking on the lake/bay. The grand daughters enjoyed the kayaking and the swimming. the only complaint from everyone was that we had to depart for our return back to SC. You have a beautiful house. thank you for allowing us to visit."
Edgewater Retreat on Little Sebago Lake - Lakefront w/Sauna & EV Charger
Luxury Carriage House a short stroll from town!
Fridge, microwave, oven, stovetop

Luxury Carriage House a short stroll from town!

2.0 star property
10.0 out of 10, Exceptional, (5)
"Amazing location and beautiful little property. Everything was immaculate and welcoming, and we felt so taken care of, down to the small touches like just the coffee we like! Communication was great and timely, too. We'll definitely be back next time we are in Maine!"
The price is AED 1,465
AED 2,250 total
includes taxes & fees
2 Mar - 3 Mar
Luxury Carriage House a short stroll from town!
Coastal Cottage in fishing Village
Terrace/patio

Coastal Cottage in fishing Village

9.2 out of 10, Wonderful, (5)
"My wife and I can not say enough good. Everything was fantastic we can't wait to visit again , everyone in the area were very nice the location was incredible.tjanknyou very much for the pleasant stay"
Coastal Cottage in fishing Village
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.
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Other property types in Chebeague Island

The Weldon Hotel
Deluxe Suite, 2 Bedrooms | Private kitchen | Full-size fridge, microwave, oven, stovetop

The Weldon Hotel

4.0 star property
9.6 out of 10, Exceptional, (38)
"Very clean and comfortable! "
The price is AED 562
AED 612 total
includes taxes & fees
16 Mar - 17 Mar
The Weldon Hotel
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (101)
"We stayed to visit family in the area. The location was excellent and we loved the ocean view. Everything was very clean, except under the sofa in the living room. We searched for a dropped puzzle piece and "
Gorgeous ocean-front home with stunning beach views
100 feet from the ocean 3 bedroom cottage 420 friendly
Interior

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly
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.