
Pet-friendly holiday rentals in Chebeague Island
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Top-rated pet-friendly home rentals in Chebeague Island
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Pet-friendly house rentals

Sunday River Bethel Village ! Walk to Restaurants
Scott's place was perfect for our small family's ski trip! It was exactly as pictured, had everything we needed for our stay, and was so close to Sunday River (~10 minutes) and right down the road from restaurants in Bethel Village. We would love to stay again on our next ski trip!

Walk to Beach from Spacious 1920 Home
First off. Let me say the house was great. It was nice and big plenty of room. Very clean we had a big gathering and everyone absolutely loved it and was very satisfied with the price they paid to stay the weekend. Even though we went during the offseason it was still a great time. We Will definetly book this Airbnb again. Thank you Krystal and we will be in contact again.

King beds-Charming Retro 3BR+Office House
This was our first experience with an Air B&B and happy that it was with Spencer. Our main reason for the East Coast trip was to see our grandsons football games at Bowdoin College and it was a perfect location. We stayed for seven weeks and loved the experience.

York River's Private Escape
We had a lovely weekend at Debbie's home! It was immaculate and very welcoming. The place is located right off the main road but is secluded. The weather wasn't great so we didn't get to enjoy the grill or outdoor setup but it looked very nice. The kitchen was amazing! All the equipment was in great condition and as a cook, was everything I wanted. Close to everything York has to offer! Great for families or a couple with a dog like us. Highly recommend!

Cheerful spacious updated 1825 Maine Farmhouse!
Second stay at the farm house. Two weeks this time. We just love it here. Plenty of space yet cozy, everything you need, lovely outdoors space. We enjooed watching the chickens, dicks and horse next door. I wish we could stay for months. Thank you, Amy and family!

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
Julie was fantastic and always responded in minutes to any questions we had. I love their home manual which is so easy to navigate and has answers for everything. The home is super cozy and the large gas fireplace downstairs was a treat on cooler April mornings. The weather wasn't on our side for 1/2 of short stay, but we had a family olympics inside, using their ping pong table, foosball and connect 4 game. We did get out on kayaks one day - lovely lake, larger than you think! tons of hiking nearby too.

Riverside
We had an amazing time over valentines day weekend. There was a snow storm and Kent snow blowed around our vehicle to make sure we could get out. The house is very comfortable and peaceful, amazing view of the river and just off the road enough to not be bothered by passing traffic. Definitely recommend!!!!

Cozy house located in West Bethel
This home was so charming. Once we were inside, we felt right at home - everything was so wisely laid out, clean, and fit my family of 4 plus 2 furry animals perfectly. The decor is beautiful! The outside had a good size yard with a runner for my dogs which was so thoughtful. The house is only 12 minutes away from Sunday River and very easy to get to. Our host was wonderful, I really appreciate her flexibility and accommodation to my several requests!! We had a blast - thank you so much!!!!
Pet-friendly home rentals with a pool

Fantastic Kittery Home with Pool
The house was perfect for my family and I- plenty of open space for the kids to play and a great yard- even in December with cold weather the kids loved the play gym outside!! The location was amazing with lots of things to do within a few minutes and the food scene was great. Thanks to Ned for a spotless home and great amenities!! We can’t wait to come back in the summer to use the pool!!

NoCo Village 1-Bedroom
Perfect stay for 4 adults, 1 infant, and 1 dog! Love the two-bedroom, two-bathroom layout, plus the kitchenette to make oatmeal and toast in the morning before hitting the ski trails. Clear check-in instructions, no hassle at all even when we arrived around midnight.

Blissful Mountain Getaway Cabin | Private Pool
Cabin is absolutely beautiful, very clean, welcoming, and beds are comfortable. Highly recommended, and we’ll be back for sure! Thanks for being awesome!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
My stay was very comfortable. The property was well kept and updated. The beds and furniture were were in perfect condition. Both the house and the grounds were exceptionally clean and well maintained. I would visit again!

Million $ views, Hot Tub, Crooked River- Private
Was a very nice peaceful getaway the home was spotless and had everything we needed plus extra great place to disconnect

Steep Falls Escape, river & falls just steps away
great accommodation, thoughtfully decorated, clean with everything you need. Perfect as a hiking base, lots of recommendations from the wonderful hosts

Lakeside cabin in the woods
Spent Thanksgiving at the cabin and it was absolutely perfect! Jim met us upon check-in with a welcome basket full of homemade baked goods—they were delicious! Home was stocked with board games and puzzles as well. 10/10 stay.

The Sugar Shack - A sweet spot in the Village
Loved our stay at the sugar shack! Perfect place for a ski trip with our pups. We enjoyed a nightly soak in the hot tub after long days on the slopes!
Private, pet-friendly home rentals

2 BDR| Fenced in Yard| Hot Tub| Bring your pup
Actually rented both units A & B of this property for my wife's birthday to have some room for additional family (surprise). Unit A was awesome! 2 beds and a bath, BIG kitchen that had everything you would need, dog friendly with a fenced in yard which is always a plus, super comfortable living room/dining room combo that had plenty of room for everyone to gather, private courtyard (shared with unit B) with room for outdoor dining and a grill PLUS hot tub! I could go on but to summarize, it was perfect for our plans. The addition of unit B gave us the whole place and I couldn't be more pleased! Centrally located. Anywhere we wanted to explore, from Kennebunkport to Ogunquit and beyond, was never more than 20 - 30 minutes away. Even the neighbors were amazing (friendly)! 100% I would (and plan to) stay here again!

Hot tub with country setting, close to village.
House was as listed, great location in a beautiful area. Plenty of amenities and host was helpful and responsive leading up to and during my stay.

Private & Spacious, 9 Miles to downtown N. Conway
This was our second stay and we are planning to make it an annual event. The house is beautiful, comfortable, cozy and well stocked. I loved cooking in the kitchen surrounded by my family. The fireplace is amazing and the location is perfect. We ski Canmore and Bretton Woods and down town North Conway is filled with great bars and restaurants and 10 minutes from the house. Perfect spot.

Quintessential farmhouse in the village
Diann's home was perfect for our "Polar Express" weekend in North Conway. We had two grown children and two grandchildren with us and the house was perfect. Loved the bedroom set-ups, dining areas, game room. Everything was clean and ready for us. The games were great for the kids and we had some snow overnight and enjoyed making "tiny" snowmen in the yard. Perfect combination of lovely decor and furnishings that were comfortable and well-built for little people. Highly recommend this location and this specific home for a winter retreat! Loved the Polar Express (recreating a trip we took 25 years ago) and an afternoon at Nestlenook Farm where we enjoyed horse-drawn sleigh magic! Thanks, Diann.

Oliver House with Sebago Lake boat access
We had an awesome weekend stay at Monique’s cottage. The house was clean and equipped with all amenities listed. The yard space is huge for backyard games. Would definitely stay here again!

All Season Wells Beach Retreat attractions close
This is the second time I’ve stayed at this house. Spacious and a lot of light. You can see the marsh from the windows, which is lovely. Near the beach. Recommend!

The Yankee Dugout
Host was great and friendly. Beautiful neighborhood. Apt was very clean and comfortable. Many extras like Keurig, coffee, tea hot chocolate and water bottles. Cozy extra blankets, fans and fireplace. Bathroom was clean and had liquid soaps, shampoo etc. Not a full kitchen, but all you need. Would definitely stay again.

Monument SWEET!
A group of 5 of us stayed at Kathy's listing and felt like we had plenty of room. We were all comfortable and found the location to be great with plenty to do within walking distance. Some of the doors were glass with blinds/shades that weren't entirely opaque so we had to be somewhat mindful when changing in our room. The front door battery was dead when we arrived and so the door was unlocked but this was quickly resolved with the help of the host and extra batteries on site. Location was fabulous and peaceful. No issues with finding free street parking, either. Overall, we enjoyed our time here and would stay at this listing again!
Quick stats about holiday rentals that are pet-friendly in Chebeague Island
Total rentals
70 properties
Nightly prices starting at
£45 before taxes and fees
Total number of reviews
2.3K reviews
Family-friendly rentals
60 properties are a good fit for families
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Destinations to explore
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- Wells Beach
- Ogunquit Playhouse
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Long Sands Beach
- Popham Beach State Park
- Purity Spring Resort
- East End Beach
- King Pine Ski Area
- Pemaquid Beach
- Parsons Beach
- Mothers Beach
- Middle Beach
- Palace Playland
- Portland Museum of Art
- Cliff House Beach
- Dunegrass Golf Club
- Ferry Beach
- Wolfe's Neck Woods State Park
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Arundel Beach