Vacation rentals in Cumberland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cumberland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Farm stay in North Yarmouth

4.96 out of 5 average rating, 110 reviews

Hobby Farm Guesthouse-17 acre trails-1 good dog OK

The Farm Stay Guesthouse sits up high with beautiful views of the meadow, pond, woods beyond, and breathtaking sunsets. The guesthouse is sunny and spacious with a queen sized bedroom. The kitchen has anything you’d need to enjoy your locally sourced Maine lobster and steamers. The property hosts lovely walking/mountain bike trails. Winter, the trails are groomed for neighborhood X-CC skiing trails! There is a Summer Sandy beach pond that transforms into a seasonal skating pond. Always fun!

Apr 17 – 24

R2,847 ZAR per night
Guest favorite

Guesthouse in Portland

4.95 out of 5 average rating, 278 reviews

Beautiful large studio on the ocean.

Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.

Apr 25 – 30

R3,008 ZAR per night
Guest favorite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Cozy heater for spring, fan in the summer. This yurt is “glampy” inside with leather chairs, pine log bed. The Island Yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Wicked good water. Seasonal restaurants. Fire pit. Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to yurt.

Jan 3 – 10

R2,359 ZAR per night

Popular amenities for Cumberland vacation rentals

Stay near Cumberland's top sights

Allagash Brewing Company156 locals recommend
Wolfe's Neck Woods State Park123 locals recommend
Eastern Promenade Trail251 locals recommend
Wolfe's Neck Oceanfront Camping5 locals recommend
Maine Audubon39 locals recommend
Buck's Naked BBQ14 locals recommend

Other great vacation rentals in Cumberland

Guest favorite

Home in Lisbon

4.94 out of 5 average rating, 328 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Feb 27 – Mar 6

R1,255 ZAR per night
Guest favorite

Guest suite in Freeport

4.96 out of 5 average rating, 114 reviews

Solar Suite surrounded by Nature

Oct 27 – Nov 3

R2,314 ZAR per night
Guest favorite

Home in Yarmouth

4.92 out of 5 average rating, 483 reviews

Beautiful Coastal Maine Getaway

Nov 20 – 27

R8,017 ZAR per night
Superhost

Home in Falmouth

4.86 out of 5 average rating, 173 reviews

Amazing Bay View Home with Hot Tub

Dec 3 – 10

R2,434 ZAR per night
Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 194 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Apr 17 – 24

R2,157 ZAR per night
Guest favorite

Guesthouse in Cape Elizabeth

4.98 out of 5 average rating, 138 reviews

Newly built private guest suite off Shore Road

May 8 – 15

R2,701 ZAR per night
Guest favorite

Cottage in Pownal

4.99 out of 5 average rating, 322 reviews

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Mar 2 – 9

R5,257 ZAR per night
Guest favorite

Home in Freeport

4.85 out of 5 average rating, 249 reviews

Home On Pond in Woods - Guest Suite

Sep 15 – 22

R1,615 ZAR per night
Guest favorite

Apartment in Yarmouth

4.96 out of 5 average rating, 92 reviews

Sweet 1-Bedroom Apartment in Vintage Village Cape

Apr 20 – 27

R2,755 ZAR per night
Guest favorite

Apartment in Yarmouth

4.94 out of 5 average rating, 50 reviews

Flower Farm Studio Apartment

Jan 25 – Feb 1

R2,003 ZAR per night
Guest favorite

Home in Cumberland

4.94 out of 5 average rating, 17 reviews

Forest Lake Cottage

Sep 30 – Oct 7

R5,448 ZAR per night
Guest favorite

Apartment in Falmouth

5.0 out of 5 average rating, 36 reviews

Sweet 2-story 1910 Bungalow near Portland, Beaches

Mar 3 – 10

R2,357 ZAR per night

Quick stats about vacation rentals in Cumberland

Total rentals

740 properties

Rentals with dedicated workspaces

360 properties have a dedicated workspace

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

220 properties allow pets

Family-friendly rentals

470 properties are a good fit for families

Total number of reviews

57K reviews

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 210 homes with a kitchen, over 160 homes with free parking, over 220 homes with wifi, over 200 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do cottage rentals in Cumberland have a kitchen?

    Absolutely! We offer over 30 cottage rentals with a kitchen in Cumberland. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Cumberland have wifi?

    Absolutely! We offer over 30 condo 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 470 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do private suite rentals in Cumberland have air conditioning?

    Absolutely! We offer over 30 private suite 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 1,450 vacation rentals in North Deering, over 1,040 vacation rentals in Saint George, over 1,750 vacation rentals in Falmouth, and over 1,410 vacation rentals in Back Cove.

  • Are there pet-friendly vacation rentals in Cumberland?

    Four-legged friends are welcome in Cumberland. Choose from more than 220 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 360 vacation rentals in Cumberland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Cumberland have free parking?

    Absolutely! We offer over 300 house rentals with free parking in Cumberland. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in private suite rentals in Cumberland?

    Experience the best of Cumberland with our private suite rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

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