
House holiday rentals in Westport Island
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Top-rated house rentals in Westport Island
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Popular amenities for house rentals in Westport Island
House rentals with a pool

Luxe Liberty: Getaway with Heated Indoor Pool!
this was the 3rd time our family has stayed,again we had a fantastic time! We chose to return due to the great space, a fabulous indoor pool, great kitchen and an amazing view. Great attention to details, comfortable for large families or groups and peaceful for just 2.

Coastal Retreat with Pool and Cheerful Vibes
We felt like at home. The house is located in a private property with swimming pool and tennis courts. It’s very clean and very peaceful. Just a clarification about the description : there’s no bathroom in the basement. Then if you come with elderly people or very young kids, it could be annoying. If you like cooking, the kitchen is very well equipped. We´ll keep a very good memory of our stay in Ducktrap Retreat during the colorful foliage season.

Lovely home with hot tub and pool
I had a wonderful stay., they were fantastic in accommodations for me and my service dog who loved the yard. The home is beautiful and the host was very accommodating. communication was great. I look forward to staying there when I’m in that area again.

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
Angela was a fantastic host, responding quickly to any questions. The home was nice, close to downtown, and a HUGE yard for the dogs

There's No Place Like Home
Kathi’s place was great! Super close to the Downtown Portland/Old Port area. Kathi was a great host, extremely responsive and genuinely nice, plus she even made my family and I some delicious blueberry muffins for our stay! Her instructions were clear and she made us feel right at home! Would definitely stay again whenever we’re in the area!

Riverfront Luxury in the woods, Million $ Views.
Jon’s cabin is a beautiful place to get away from it all. Very comfortable and well designed. We had everything we needed to cook and hole up for a few days. If you decide to drive to the lake, I would recommend 4WD. We had a truck but were not aware of how soft the ground was and ended up needing to be towed out. Still highly recommend! Enjoy your stay!

OOB Oasis - 5BR private Retreat w/ Pool
Great house! Very spacious, plenty of bathrooms, and fantastic location. Very easy to communicate with the owners and check in/out was simple. My minor only critique is that we wish the grill were a bit bigger and nicer. We wanted to grill one day, but we were a little disappointed and unable to do so due to the grill quality. Would definitely stay again!

Dreamy Indoor Pool/Hot tub/Sauna Near Beaches
Top notch spot and host!! We had such a great time at Alexa’s lovely home! It was so cozy, beautifully decorated, modernized, and had all the essential items you’d need - plus it is completely pet friendly! Our dog loved the fenced in yard with a doggy door to get out to it. The sauna, endless pool, and hot tub are just amazing amenities to have on site - that sunroom was my favorite place in the house to say the least! Can’t say enough about it and Alexa, too! She is super friendly, responsive, and had great recommendations for fun and good food in the area. Overall, it was just a wonderful and relaxing experience for our first time on the Maine coast and we can’t wait to visit again!
Weekly house rentals

Damariscotta River Cottage-Private location
We stayed for a long weekend and really enjoyed how peaceful the location was. Beautiful view from the kitchen & living room. Had all the needed amenities to feel at home. It’s your typical Maine Camp, cozy and rustic, but clean and comfortable. Loved that our dog was able to come along to enjoy the weekend with us. (I will note there are alot of ticks on the property so make sure you give your pup a check when they come inside. We pulled a few off each time he went out, they were teeny tiny! Not unusual for wooded areas in New England) The living room furniture wasn’t super comfortable so we ended up spending most of our time sitting at the dining table. We had a rainy, cool weekend so did more inside lounging than expected. Overall it was a great stay and we would recommend it to anyone looking for a peaceful, mid-coast Maine trip.

Kens Cottage in Round Pond ME
Wow. What a beautiful cottage on a beautiful bay in a beautiful state. Wonderful host and super convenient to northern and southern spots of Maine to visit. Everyone is nice and kind in Round Pond.

Bayville Little House on the Bay
We enjoyed our stay in Alina’s cottage. It’s in a small village with other oceanfront homes. The cottage is new with all amenities but ‘fits in’ with other established homes around it which are original to the location. We enjoyed sitting on the deck in the morning with our coffee. The cottage is dog friendly with quiet neighborhood roads to walk. It’s an easy drive to Boothbay Harbor & other points of interest. If you are looking for a peaceful getaway, Alina’s is the place for you!

Unique Octagonal House with Private Beach!
Simply magical! Cozy and fun space. We enjoyed watching eagles and ospreys fish, seals pop their heads up, and even an adorable family of foxes from the comfort of the living room! Kitchen had all necessities for cooking most meals at home. A nice trail for walking down the road and an awesome beach where the kids threw stones and searched for seaglass each afternoon. We were all sad to leave!

The Rowe House
Our stay at The Rowe House was absolutely wonderful! The space was immaculate, and had every amenity we needed. The host was welcoming and made us feel at home. The location was perfect - close to everything yet peaceful and relaxing. We especially loved the kitchen that led to the side porch. The yard was well taken care of and had plenty of seating to hang out. Also the beds were very comfortable. It was truly one of the best Airbnb experiences we’ve had, and can’t wait to return. Highly recommend to anyone looking to stay in Boothbay Harbor. Beautiful location!

Modern Coastal Bungalow • 3BR/2BA • Walk to Town!
We had a great time in Boothbay Harbor. We Loved the house and it's location. highly recommend staying. The weather was exactly what we wanted coming from Florida.

Lakeview House
We had a wonderful stay at Florin’s Airbnb and would happily stay again! Everything was clean and comfortable, just as was described on the listing. Florin is also friendly and very responsive. Great stay!

Romantic Mirror cabin in the woods
Just spent a couple of nights at Hidden Pines Cabins in South Berwick, Maine and had the most romantic and relaxing experience. We chose the mirrored cabin because of its uniqueness and it was perfect for us. Keep in mind this is a one room cabin with a small bathroom, but plenty for two adults. We loved the private jacuzzi and sauna and used it regularly after our hikes. As for the host Christian, he was probably the best host I’ve EVER dealt with using an Airbnb. Friendly, responsive and welcoming! He does have two other cabins the Pond View and the A Frame. We plan on renting the A Frame sometime in the winter. Thank you, Christian! 💕 Barbara
Private house rentals

Charming Boothbay Cottage
Cuter and bigger than anticipated from photos. Had everything we needed. A few areas needed a bit more TLC, but overall we were very satisfied. Thank you!

The Happy Harbor House-Walk to town!
Liz is a phenomenal host The home is newly remodeled and beautiful! It’s litterally steps away from the waterfront. She gave us lots of suggestions which we did including a stop in Camden on our way from BarHarbor for lunch at Camden deli and views from mt battie. We visited Maine Coastal Gardens and enjoyed the trolls and lush gardens (wish we could have stayed longer) and did a 4 1/2 hour whsle/ puffin tour no whale sittings but we saw lots of puffins, a seal and porpoise. Ended the day with dinner at ports of Italy Amazing food We would definitely stay here again only regret is we didn’t stay long enough

Amazing view, eagles, hot tub, 1 mi walk from Bath
Sometimes photos just don't do the real thing justice, and this is the case with this property. The property and the views are truly spectacular! The home is huge and has everything you could ever need to live for a week or more. The porch, especially the screened in portion are magnificent and the hot tub was a perfect way to finish up a great day. We had so many plans to adventure out, but found ourselves wanting to stay and enjoy the pristine yard or just sit on the porch and enjoy each others company, we didn't want or need to leave. Having coffee and watching eagles fly by over the river was truly spectacular. Judy is one of the nicest, easiest hosts we have had the pleasure to work with and truly appreciates your patronage. And Hugh's journal on all things Graywood is a lifesaver. Not only would we return again, but we look forward to it.

Family Escape w/ Kayaks, Fire Pit, & Water Access
What a whimsical town! In the middle of nowhere So peaceful Yet, Wallace's General Store, right up the road Maybe a mile Amazing food and Sandwiches and just about everything under sun to Need So, just down the road is this Amazing Place! Three Sisters Farm Heaven Awaits Must check out

Boothbay coastal home
I can't express enough how beautiful Jasmine's cabin is. Even though the cabin is located not too far from the main street, but it's still excluded and I felt like remote. Proximity to other places is amazing, minutes away to Botanical Gardens and the Cabbage Island Clambake. The kitchen had everything I need to cook quick meals for my family, above and beyond, not just the "basic" condiments :). Thanks so much for offering this place and making our trip more special. I'll stay here again and again when we visit Boothbay. THANK YOU!

Maine Stowaway Carriage House
Perfect in every way! I have stayed at multiple air BnB’s and nothing compares to this house! Pictures do not do this place justice!! The location is awesome, secluded with a great view. One thing that stood out to me other than the awesome view and being secluded is that the house is stocked with everyday household essentials, other air BnBs I have stayed at never had the house stocked they way that this one does! I highly recommend this house to anyone that wants to visit south port!

Laurel Shore Cottage - Waterfront, Pet friendly!
Our stay at Laurel Shore Cottage was just what we needed. The location was serene - and we spent most afternoons and evenings sitting on the porch soaking in the beautiful landscape and scenery. The cottage itself was uncluttered and comfortable and the host was very responsive.

Naturalist Paradise on the Cove
Beautiful setting. Great host. Quiet. Tranquil. Peaceful. Once we navigated the dirt road we enjoyed the drive to restaurants. Into Bath. Reid State park was amazing. We liked The Osprey. We loved Blue at Grey Havens.
Quick stats about house rentals in Westport Island
Total rentals
30 properties
Total number of reviews
580 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Sebago Lake
- Scarborough Beach
- Popham Beach State Park
- Surfside Beach
- Samoset Resort
- Pemaquid Beach
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- East End Beach
- Cliff House Beach
- Brunswick Golf Club
- Belgrade Lakes Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
- Funtown Splashtown USA
- Ferry Beach
- Dunegrass Golf Club
- Wolfe's Neck Woods State Park
- Freddy Beach
- Portland Museum of Art
- Crescent Beach State Park
- Maine Maritime Museum
- Prouts Neck Country Club
- Bradbury Mountain State Park