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.

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Guest favorite

Farm stay in North Yarmouth

4.96 out of 5 average rating, 111 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!

Dec 30 – Jan 6

G$37,346 GYD per night

Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 111 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

Oct 6 – 13

G$23,434 GYD per night

Guest favorite

Loft in Freeport

4.97 out of 5 average rating, 194 reviews

Cozy & Private Studio Apartment (Pet Friendly!)

Recently renovated studio apartment, very cozy, with a private side yard and entrance, kitchenette and TV (Cable, Netflix, Disney Plus, Hulu and Amazon). Very comfortable queen size bed with floor space for kids if desired. Fantastically located just over a mile from beautiful Winslow Park's walking trails and beach, four miles south of downtown Freeport's shopping and 15 miles north of the popular city of Portland. Housebroken and well behaved pets welcome to join their humans!

Jun 7 – 14

G$29,312 GYD per night

Guest favorite

Apartment in Freeport

5.0 out of 5 average rating, 130 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

Welcome to our spacious 1000 sq. ft. Maine barn apartment! This bright and comfortable retreat is the perfect base for exploring all that Maine has to offer. Enjoy the fully-appointed kitchen, equipped with everything you need. The quiet bedrooms feature memory foam beds for a restful sleep, and the private bathroom boasts a spacious shower. Please note that we have a no-pet policy due to allergies. Book your stay today and experience the best of Maine! Registration #: STRR-2021-24

Oct 14 – 21

G$39,973 GYD per night

Guest favorite

Cabin in Freeport

4.98 out of 5 average rating, 469 reviews

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

May 14 – 21

G$32,704 GYD per night

Guest favorite

Apartment in Portland

4.93 out of 5 average rating, 552 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Jan 5 – 12

G$20,047 GYD per night

Guest favorite

Home in Cumberland

4.95 out of 5 average rating, 279 reviews

Rustic charm close to Portland

Peaceful and private. My home is a country getaway with unique charm and has a feeling like no other. Just voted the safest town to live in Maine, located close to downtown Portland, the Portland Jet Port, Freeport, beautiful Maine beaches, apple orchards, a Gorgeous wedding venue a mile away called Caswell Farm and close to trails for hiking, my home has many options. It's a great spot for a family to stay and the rental is the entire home.

Mar 7 – 14

G$39,426 GYD per night

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 217 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Jul 7 – 14

G$26,445 GYD per night

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 151 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

Sep 16 – 23

G$24,060 GYD per night

Guest favorite

Guesthouse in Cumberland

4.97 out of 5 average rating, 152 reviews

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

Jun 20 – 27

G$62,653 GYD per night

Guest favorite

Guest suite in Freeport

4.95 out of 5 average rating, 195 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

May 18 – 25

G$14,554 GYD per night

Guest favorite

Farm stay in Gray

4.94 out of 5 average rating, 246 reviews

Great Goat Get-away in Southern Maine!

This quiet and cozy house is located in the woods at the renowned Ten Apple Farm. Centrally located in Southern ME, we're just a short drive from Portland, lakes, ski areas, LL Bean and more! On the farm you can meet and interact with our herd of goats, sheep, pigs and chickens, learn to milk, collect eggs, and arrange on of our famous goat hikes!

Feb 7 – 14

G$29,961 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cumberland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Mackworth Island State Park130 locals recommend

Buck's Naked BBQ14 locals recommend

Other great vacation rentals in Cumberland

Superhost

Apartment in Portland

4.78 out of 5 average rating, 303 reviews

Studio w/ Patio, Sauna & Onsite Massage

Sep 5 – 12

G$22,547 GYD per night

Guest favorite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

Sep 17 – 24

G$31,559 GYD per night

Guest favorite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Jul 22 – 29

G$28,725 GYD per night

Guest favorite

Home in Freeport

4.99 out of 5 average rating, 163 reviews

"The Cozy Cottage in the heart of Freeport Village

Jan 22 – 29

G$26,903 GYD per night

Guest favorite

Home in Freeport

4.94 out of 5 average rating, 205 reviews

The Outlet House, Comfortable Cottage

Sep 26 – Oct 3

G$32,254 GYD per night

Guest favorite

Guesthouse in Cumberland

4.94 out of 5 average rating, 82 reviews

Cozy & Convenient Cumberland Guest Cottage

Apr 29 – May 6

G$29,563 GYD per night

Guest favorite

Apartment in Yarmouth

4.96 out of 5 average rating, 93 reviews

Sweet 1-Bedroom Apartment in Vintage Village Cape

Oct 6 – 13

G$33,157 GYD per night

Guest favorite

Apartment in Falmouth

5.0 out of 5 average rating, 38 reviews

Sweet 2-story 1910 Bungalow near Portland, Beaches

Mar 2 – 9

G$25,978 GYD per night

Show all

Quick stats about vacation rentals in Cumberland

Total rentals
730 properties
Rentals with dedicated workspaces
360 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
220 properties allow pets
Family-friendly rentals
450 properties are a good fit for families
Total number of reviews
56K reviews

Frequently Asked Questions

What are the most popular amenities for Guesthouse Rentals in Cumberland?
Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do private suite rentals in Cumberland have a kitchen?
Absolutely! We offer over 10 private suite rentals with a kitchen in Cumberland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cumberland have wifi?
Absolutely! We offer over 320 house 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 450 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Cumberland have air conditioning?
Absolutely! We offer over 200 apartment 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 1,070 vacation rentals in Saint George, over 1,430 vacation rentals in Back Cove, over 1,470 vacation rentals in North Deering, and over 1,760 vacation rentals in Falmouth.
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 cottage rentals in Cumberland have free parking?
Absolutely! We offer over 30 cottage rentals with free parking in Cumberland. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Cumberland?
Experience the best of Cumberland with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Vacation rentals in Cumberland

Top-rated vacation rentals in Cumberland

Vacation rentals for every style

Houses

Apartments

Cottages

Popular amenities for Cumberland vacation rentals

Stay near Cumberland's top sights

Other great vacation rentals in Cumberland

Apartment in Portland

Tiny home in Portland

Yurt in Chebeague Island

Home in Freeport

Home in Freeport

Guesthouse in Cumberland

Apartment in Yarmouth

Apartment in Falmouth

Quick stats about vacation rentals in Cumberland

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

What are the most popular amenities for Guesthouse Rentals in Cumberland?

Do private suite rentals in Cumberland have a kitchen?

Do house rentals in Cumberland have wifi?

Are there family-friendly vacation rentals in Cumberland?

Do apartment rentals in Cumberland have air conditioning?

Where should I stay in Cumberland?

Are there pet-friendly vacation rentals in Cumberland?

Are there vacation rentals with a dedicated workspace in Cumberland?

Do cottage rentals in Cumberland have free parking?

How much does it cost to stay in apartment rentals in Cumberland?

Destinations to explore