Holiday houses in Cumberland

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Popular amenities for Cumberland holiday rentals

Stay near Cumberland's top sights

Hannaford Supermarket280 locals recommend
Eventide Oyster Co.271 locals recommend
L.L. Bean Factory Store270 locals recommend
Peaks Island176 locals recommend
Eastern Promenade Trail251 locals recommend
Duckfat172 locals recommend

Other great holiday rentals in Cumberland

Top Guest favourite
Home in Old Orchard Beach
5 out of 5 average rating, 13 reviews

Stunning Beachfront Dream Home

TomRating, 5 stars1 week ago
We had a great stay, the house exceeded our expectations. The views from the second and third floors were unbelievable. The house was clean and wonderfully laid out. There was just two of us and even with the large living space, we felt right at home and couldnt have asked for a better staycation. It was our first time in Old Orchard out of season and recommend both this house and the town of Old Orchard before the crowds arrive, it was an entirely different experience with with it being out of season.
Guest favourite
Home in Scarborough
4.93 out of 5 average rating, 59 reviews

Gorgeous 4 BR home with HOT TUB

ShellyRating, 5 stars1 week ago
Gregory's place was great for our 2 night getaway. Hot tub was amazing and private from neighbors. Bathrooms and kitchens were well stocked. I will definitely go back for another getaway
Guest favourite
Cabin in Greenwood
4.92 out of 5 average rating, 13 reviews

All seasons Lake House next to ski areas

GeorgeRating, 5 stars6 months ago
Had a great stay at the cabin. The lake and surrounding mountains are beautiful. Lake was fun to fish off dock and using canoe. Nearby town Bethel has a few nice restaurants and there are a number of easily accessible day hiking spots nearby. The beds are super comfortable as well. Overall a great stay!
Superhost
Home in Newcastle
4.91 out of 5 average rating, 32 reviews

Spring into the season eating lobsters w/friends

MarceloRating, 5 stars7 months ago
Very nice place to stay big nice and clean recommended this place to everyone looking for a good place big and clean this the right place
Top Guest favourite
Home in Gray
4.97 out of 5 average rating, 63 reviews

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars4 months ago
The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.
Superhost
Cabin in Bartlett
4.92 out of 5 average rating, 179 reviews

Mountain View Retreat, Near skiing, shopping

JaimeRating, 5 stars3 months ago
We absolutely loved our stay! Plenty of room for 8 guests (and more!!) in a beautiful setting. There was many helpful amenities, like kitchen items, and plenty of towels. The location is perfectly centered to many popular things to do. James was always very responsive to questions left clear instructions. We highly recommend staying here and hope to do so again in the future.
Superhost
Townhouse in Bartlett
4.85 out of 5 average rating, 105 reviews

Spacious Family Vaca Storyland*Saco*Close to all!

JoanneRating, 5 stars2 months ago
Great place to stay. The basement space for the kids is great, they each had their own bedroom but could hang in the common space. Golden Tee was a HIT! Centrally loacated to multiple ski mountains. Plenty of room to spread out and get comfortable!
Guest favourite
Home in Ogunquit
4.92 out of 5 average rating, 38 reviews

Ogunquit Beach House - New Listing -Great Location

GinaRating, 5 stars8 months ago
This house is everything and more. Amazing location, plenty of room, comfortable and clean. We had a blast. Close walk to town and beach. Aaron had plenty of beach chairs and a beach carrier for all your stuff. Plenty of space to park, grill, AC in all rooms. Was fantastic. Can’t wait to be back!

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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  4. Cumberland County
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