Vacation rentals in Cumberland
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Top-rated vacation rentals in Cumberland
Guests agree: these stays are highly rated for location, cleanliness, and more.
Farm stay in North Yarmouth
4.96 out of 5 average rating, 110 reviewsHobby 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
Guesthouse in Portland
4.95 out of 5 average rating, 278 reviewsBeautiful 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
Yurt in Chebeague Island
4.97 out of 5 average rating, 101 reviewsYurt 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Cumberland vacation rentals
Other great vacation rentals in Cumberland
Home in Lisbon
4.94 out of 5 average rating, 328 reviewsUnplug at a Beachy Bolthole with Classic New England Style
Feb 27 – Mar 6
Guest suite in Freeport
4.96 out of 5 average rating, 114 reviewsSolar Suite surrounded by Nature
Oct 27 – Nov 3
Home in Yarmouth
4.92 out of 5 average rating, 483 reviewsBeautiful Coastal Maine Getaway
Nov 20 – 27
Home in Falmouth
4.86 out of 5 average rating, 173 reviewsAmazing Bay View Home with Hot Tub
Dec 3 – 10
Apartment in Gorham
4.96 out of 5 average rating, 194 reviewsCozy Private 1 Bedroom Apartment - Gorham Village
Apr 17 – 24
Guesthouse in Cape Elizabeth
4.98 out of 5 average rating, 138 reviewsNewly built private guest suite off Shore Road
May 8 – 15
Cottage in Pownal
4.99 out of 5 average rating, 322 reviewsUpscale Timber-Frame Cottage, Shop/Dine/Hike/Bike
Mar 2 – 9
Home in Freeport
4.85 out of 5 average rating, 249 reviewsHome On Pond in Woods - Guest Suite
Sep 15 – 22
Apartment in Yarmouth
4.96 out of 5 average rating, 92 reviewsSweet 1-Bedroom Apartment in Vintage Village Cape
Apr 20 – 27
Apartment in Yarmouth
4.94 out of 5 average rating, 50 reviewsFlower Farm Studio Apartment
Jan 25 – Feb 1
Home in Cumberland
4.94 out of 5 average rating, 17 reviewsForest Lake Cottage
Sep 30 – Oct 7
Apartment in Falmouth
5.0 out of 5 average rating, 36 reviewsSweet 2-story 1910 Bungalow near Portland, Beaches
Mar 3 – 10
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
- Portland Vacation rentals
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- Pet-friendly rentals Cumberland
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