Holiday rentals in Cumberland

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Popular amenities for Cumberland holiday rentals

Other great holiday rentals in Cumberland

Top guest favourite
Home in Yarmouth
5 out of 5 average rating, 11 reviews

Peaceful retreat in Yarmouth

AlexRating, 5 stars1 week ago
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!
Top guest favourite
Cabin in Freeport
5 out of 5 average rating, 49 reviews

The Maine Frame: Cozy Firepit 7 Min to L.L. Bean

MichaelRating, 5 stars1 week ago
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!
Guest favourite
Flat in Gray
5 out of 5 average rating, 7 reviews

Bright and Cozy Studio

KatherineRating, 5 stars2 days ago
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.
Guest favourite
Flat in Falmouth
4.9 out of 5 average rating, 88 reviews

Peaceful & Cozy Falmouth Getaway

MadelynRating, 5 stars1 week ago
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! :)
Top guest favourite
Guest house in Yarmouth
4.99 out of 5 average rating, 140 reviews

Private Guesthouse in the Woods

RachelRating, 5 starstoday
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!
Superhost
Flat in Yarmouth
4.8 out of 5 average rating, 20 reviews

Sunny 1 bedroom with free onsite parking

MarionRating, 5 stars10 months ago
Kellie’s home was welcoming and lovely to stay at. Perfect for our short trip home!
Top guest favourite
Treehouse in Pownal
4.98 out of 5 average rating, 101 reviews

The Copper Fox Treehouse

RebeccaRating, 5 stars2 weeks ago
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! 🦊
Farm stay in Gray
4.84 out of 5 average rating, 308 reviews

The Retreat at Crystal Lake Farm

AmieRating, 5 stars2 weeks ago
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 holiday 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

Destinations to explore

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  3. Maine
  4. Cumberland County
  5. Cumberland