
Pet-friendly vacation rentals in Cumberland
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Top-rated pet-friendly home rentals in Cumberland
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Popular amenities for Cumberland pet-friendly home rentals
Pet-friendly house rentals

Oak Leaf
Très bon séjour dans ce petit chalet au bord de la rivière.

Quiet and Private in Oxford Hills – Dog Friendly!
Amazing place, host was super kind and accommodated my family’s last minute booking since we were cancelled on twice that week! We are super happy we found this adorable beautiful place that ended up being better than the other places would have been anyway!

Hilltop Retreat with Hot Tub & Sauna near Downtown
My friend and I spent our momcation here and it was perfect! The sauna and hot tub felt relaxing. The lilacs were in bloom and smelled heavenly. The birds sang for us every morning while we enjoyed our coffee on the deck. I love to cook and the kitchen had what I needed. The house was clean and was the sweetest little set-up.

Gorgeous Studio on the Kennebec
Perfect weekend retreat for a small family with a young one. Close to downtown, museum, and the firepit was so nice at night. 5 stars all around and will return in the future. Thanks Phillip!

East End Unit
My wife, myself and our pup loved our time at Christine’s. Thought it was a great value for the area and we appreciated how many little extras were included (snacks, beer, wine, seltzer, toiletries). Location is great for walks to East Prom or Old Port, and parking is a breeze with the dedicated driveway. It is a cozy fit if you’re a bigger person (I’m 6’ and I had just a few inches of clearance from the ceiling).

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!
Bellissimo soggiorno in luogo incantevole. la casa è calda, accogliente, spaziosa, bene arredata, con gusto e classe. La vista è meravigliosa. Siamo stati benissimo!!!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
We had a wonderful stay in Angela’s beautiful home. It had great amenities, was super clean, and had everything we needed. Loved the pool and fire pit. The kitchen was roomy for cooking too. 5 stars!

Stunning Ocean Views From This Peaks Island Home
Such a great little spot in one of the nicest corners of Peaks Island! John was great, being flexible with me when my arrival time needed to be changed up. Would visit again and again!
Pet-friendly home rentals with a pool

Storyland, golf, hiking, kayak and more
We had a lovely stay at the condo. It was the most comfy place to get snowed in. We received about a foot of snow the night we checked in and Seasons was very helpful to continually plow and shovel walkways. We explored the property and had fun sledding down hills with our tube. The condo is very clean and comfortable and has everything you may need. It was still decorated for the holidays which was a nice touch as well. The electric fireplaces worked great and were so pretty to look at. All of the furniture was very cozy and comfortable. The carpet throughout is great on cold days. We highly recommend a sleigh ride at Nestlenook farm if staying in the winter. Living Shores Aquarium is down the block and a great place to visit with kids. Diana’s Baths is a short drive away and beautiful to explore in the snow. Our daughter loved seeing the frozen waterfall. There are lots of restaurants nearby. We can’t wait to come back and see it during the summer months.

Attitash Retreat
Had a great time peaceful get-away with great mountain views. Climbing,swimming,snowboarding, and all outdoor sports within close distance. I would definitely stay again

Spacious Condo-Attitash Ski-Storyland-Saco & More!
Beautiful place to stay! Great amenities for the kids ! Will definitely go back ❤️

Cozy Top Floor-1 King, Mtn View, Jetted Tub, Pools
The place was so clean, quiet and peaceful. Secluded but so much to do in a short area. Can’t say enough good things. Will be coming back.

Bartlett N. Conway, NH condo ski near Storyland
We loved our stay and couldn't have felt more at home. Condo has everything you need and the hosts were so kind. Plenty of space for our family of 4 but could easily fit 6. Location is ideal for families to explore all Bartlett has to offer. Highly recommend and can't wait to come back!

Spacious N Conway Retreat | Hike, Ski, Swim, Bike
Perfect for our group of 4, plenty of space. Much bigger than I thought after viewing the pictures. Everything was clean and worked great. We took full advantage of the kitchen and there were plenty of cook and eat ware. Quick 4 minute drive to Attitash, close enough to go home for lunch. Loved that we were able to bring our dog too! Check in and check out were super easy. We will certainly be back next Winter for our Attitash weekend. Highly recommend staying with Lory for your North Conway, Attitash, Storyland, or Wildcat vacation. Thank you Lory!

An Amazing Mountain Getaway!
My family and I had an amazing weekend. Melissa was very responsive and flexible with checking in/out. Everything was clean, plenty of linens and towels, great location, comfy beds. 10/10. We can’t wait to be back!

Cabin on the hill!
Loved this cabin! The family and I enjoyed our trip to Maine. Eric was an incredible host, clear instructions for check in & check out. Will definitely book again when we head up north. Thank you ☺️
Private, pet-friendly home rentals

Charming Coastal Home
Central location, but was surprisingly very quiet and private. Kelsey is an excellent communicator and host.

Hobby Farm Guesthouse-17 acre trails-1 good dog OK
This was a lovely place to stay. We traveled with our dog, and it was the perfect place to visit with a four-legged friend. Heather's property is beautiful, and there are fun, quiet trails to traverse. It is only a short drive from Portland, Freeport, and amazing outdoor adventures. The apartment is clean and spacious. I highly recommend for your next Maine adventure.

Quiet, Comfy & Spacious Studio & Private BA
We really enjoyed our stay here! It was close to Caswell farms which we were at for a wedding. Alison was so kind and helpful. She went above and beyond to make sure we had what we needed! Would absolutely stay here again.

Forest Lake Cottage
GREAT FIND!! Don & Nina were fantastic hosts! We LOVED the location. We were welcomed with fresh flowers in a vase on the dining table, and we enjoyed our meals together there as well. We greatly appreciate how CLEAN the entire place was. The setup of their place was just perfect for us and our parents! We love to coo k, and the kitchen is well-appointed! The beds and pillows were very comfortable giving us a good night's sleep each night. The full-sized bedroom has a mini split which adds to the warmth or cool (whichever is needed). The master bedroom with a queen bed is large and comfortable. Our parents loved the two rocking chairs, and we enjoyed the comfy couch and chair. Even though we didn't have the greatest weather during our stay, we were able to get out on a kayak and enjoy the lake. The house is nestled in a very quiet cove on the lake and, because there is no public access to the lake, the entire lake is a fantastic find! This will be an annual stay for us now!

King Size Bed - Little House On Lincoln Street
Great place and a great location! Really easy to walk to downtown and some local restaurants and pubs. Would definitely recommend it for anyone wanting to stay in the area. So many good books to read if you have an extended stay.

Cozy Private Luxury Yurt Mt View/HOT TUB / Wi-Fi
This was the first time we’ve ever rented a yurt. We would definitely go back to see Shari. She did not miss a beat. It was everything that we needed right there. Even bathrobes. I highly recommend going to stay here. We will definitely be back. If I could give 100 stars I would.

Water views, privacy, decks, minutes to Portland
Haj was the best host. Giving us (and the dog that didn’t come) the nicest welcome. The house is beautiful, clean, well-equipped in a gorgeous private setting. Many thanks to our hosts for a memorable family weekend!

Modern space w private entrance, garage & laundry
Rachel’s place was extremely clean and comfortable. It was the perfect place to spend a snowy and stormy day with our pup. Very convenient to get to Portland. Close to grocery store and anything you might need. Rachel was very quick to respond when we had questions and had ice melt delivered for us same day which was a huge help in the storm.
Quick stats about vacation rentals that are pet-friendly in Cumberland
Total rentals
50 properties
Total number of reviews
2.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Beach
- Popham Beach State Park
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Coastal Maine Botanical Gardens
- East End Beach
- Cranmore Mountain Resort
- Palace Playland
- Ferry Beach
- Cliff House Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Purity Spring Resort
- Diana's Baths
- Ogunquit Playhouse
- Funtown Splashtown USA