
Vacation rentals in Cumberland
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Top-rated vacation rentals in Cumberland
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Popular amenities for Cumberland vacation rentals
Other great vacation rentals in Cumberland

Peaceful retreat in Yarmouth
Tucked away on a quiet cul-de-sac, this rental offered the perfect peaceful escape. The property sits on a huge green lot, surrounded by nature and total tranquility. We had a wonderful time unwinding here. Cydney was a fantastic host—friendly, responsive, and thoughtful. Everything about our stay was easy and relaxing. We’d absolutely rent again!

The Maine Frame: Cozy Firepit 7 Min to L.L. Bean
We were in awe as we walked into the Maine Frame - the photos are gorgeous and even they don't do it justice. What a beautiful and intentionally built cabin. We loved the spaciousness of both the inside and the outside: the high ceilings, huge windows, and large deck - all were just wonderful. The water softener system was such a delightful surprise! We loved how accessible the cabin is to downtown Freeport and had fun checking out all of the shops. We also had a beautiful drive to Harpswell for a delicious meal at the Dolphin Marina & Restaurant, and got to walk around Brunswick as well. We highly recommend the Maine Frame!

Bright and Cozy Studio
Clean beautiful little studio. Had everything you’d need including coffee! Comfortable bed and everything was very tidy and homey. Very responsive hosts as well.

Peaceful & Cozy Falmouth Getaway
This BnB was perfect - about 15 minutes from Portland. It was super peaceful, and we felt right at home; we never felt unsafe. The people in the area were also very kind and helpful as we didn’t know much about the area! :)

Private Guesthouse in the Woods
We had a great stay here! The place was perfect location and in a very nice area. Very quiet and close by to a lot of things. Also, very clean!

Sunny 1 bedroom with free onsite parking
Kellie’s home was welcoming and lovely to stay at. Perfect for our short trip home!

The Copper Fox Treehouse
We really enjoyed our stay at the treehouse. My eight-year-old loved to read in every nook of the house, so even though the weather was not ideal during our trip, because the house was so lovely and cozy, we still really enjoyed our time in Maine. I also appreciated all of the card and board games available and then on the sunny day that we had right before we left, we got to hike Bradbury and it’s a small hike, but it is so nice that it’s right outside the house and so we did it twice. Heidi was so helpful and responsive during our stay and right before we checked in. I really hope that we can come back in the future! 🦊

The Retreat at Crystal Lake Farm
Jonathan was very communicative and a great host. Depending on needs I would stay here again. We were there for a graduation at Bates College. I would recommend this place for fall stays, hikes or visiting the near by lake. It's kind of far from Bates and Portland to make it super convenient to visit those places. Overall it was a very good value and Jonathan was a fantastic host, oh and the place was clean.
Quick stats about vacation rentals in Cumberland
Total rentals
170 properties
Total number of reviews
7.2K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Frequently Asked Questions
What are the most popular amenities for Guesthouse Rentals in Cumberland?
Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Cumberland have a kitchen?
Absolutely! We offer over 20 apartment rentals with a kitchen in Cumberland. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Cumberland have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Cumberland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Cumberland?
Cumberland has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Cumberland have air conditioning?
Absolutely! We offer over 70 house rentals with air conditioning in Cumberland. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Cumberland?
Make yourself at home in Cumberland by choosing from our most frequently booked neighborhoods. We have over 1,360 vacation rentals in Back Cove, over 1,030 vacation rentals in Saint George, over 1,700 vacation rentals in Falmouth, and over 1,410 vacation rentals in North Deering.
Are there pet-friendly vacation rentals in Cumberland?
Four-legged friends are welcome in Cumberland. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Cumberland?
Yes! Work meets play with ease at over 80 vacation rentals in Cumberland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Cumberland have free parking?
Absolutely! We offer over 20 apartment rentals with free parking in Cumberland. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Cumberland?
Experience the best of Cumberland with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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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