Vacation rentals in Cumberland

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Popular amenities for Cumberland vacation 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 vacation rentals in Cumberland

Top guest favorite
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 favorite
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 favorite
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 favorite
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 favorite
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 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 Apartment Rentals in Cumberland?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with air conditioning, 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 guesthouse rentals in Cumberland have wifi?

    Absolutely! We offer over 10 guesthouse 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 1,030 vacation rentals in Saint George, over 1,410 vacation rentals in North Deering, over 1,700 vacation rentals in Falmouth, and over 1,360 vacation rentals in Back Cove.

  • 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 guesthouse rentals in Cumberland?

    Experience the best of Cumberland with our guesthouse rentals, starting at about $90 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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