Vacation rentals in Cumberland

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Top-rated vacation rentals in Cumberland

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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.

Feb 6 – 13

G$25,936 GYD per night

Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 113 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 11 – 18

G$18,959 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

May 25 – Jun 1

G$38,198 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 8 – 15

G$31,352 GYD per night

Guest favorite

Apartment in South Portland

4.95 out of 5 average rating, 167 reviews

Comfortable apartment near Willard Beach!

This luxurious first floor apartment is filled with sunshine all day long and on chilly nights the gas fireplace provides a warm ambiance. We think you’ll especially enjoy sinking into the velvet covered king size bed at night and stepping into the spacious shower that includes a rainfall shower head along with a handheld ... use either or both, as you please! The kitchen is equipped with quartz countertops, solid cherry cabinets and high end stainless steel appliances.

May 5 – 12

G$24,688 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$32,625 GYD per night

Guest favorite

Yurt in Cumberland

4.94 out of 5 average rating, 154 reviews

Tree Yurt

The Tree Yurt is quite literally a yurt in the trees. Surrounded by nature, this is YEAR ROUND glamping close to Portland. There is no running water except an outdoor sink in the warmer months. Typically May through October. A main house sits closer to the driveway and There is a chance the house and the yurt will be rented out at the same time. The yurt is about 200 feet from the house and the only shared space is the driveway, so it is actually very private.

Oct 13 – 20

G$22,828 GYD per night

Guest favorite

Apartment in Portland

4.93 out of 5 average rating, 556 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.

Dec 8 – 15

G$19,999 GYD per night

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 218 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.

May 29 – Jun 5

G$26,381 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.

Jun 13 – 20

G$24,002 GYD per night

Guest favorite

Guesthouse in Cumberland

4.97 out of 5 average rating, 153 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.

Jul 1 – 8

G$64,184 GYD per night

Guest favorite

Guest suite in Freeport

4.95 out of 5 average rating, 198 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$14,519 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

Guest favorite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

May 30 – Jun 6

G$31,567 GYD per night

Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 431 reviews

Harpswell Studio on Waterview Property! Lobster!

May 10 – 17

G$27,955 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

Nov 12 – 19

G$29,836 GYD per night

Guest favorite

Loft in South Portland

5.0 out of 5 average rating, 107 reviews

Serene studio apartment, close to everything.

G$25,345 GYD per night

Guest favorite

Apartment in Portland

4.85 out of 5 average rating, 438 reviews

Cozy, Private Apartment

Nov 23 – 30

G$25,772 GYD per night

Guest favorite

Guesthouse in Cumberland

4.94 out of 5 average rating, 82 reviews

Cozy & Convenient Cumberland Guest Cottage

May 3 – 10

G$29,492 GYD per night

Guest favorite

Apartment in Yarmouth

4.96 out of 5 average rating, 94 reviews

Sweet 1-Bedroom Apartment in Vintage Village Cape

Sep 7 – 14

G$33,260 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

Jan 1 – 8

G$25,915 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 Private Suite Rentals in Cumberland?
Enhance your stay in our Private Suite Rentals with the most popular amenities: over 10 homes with a kitchen, over 20 homes with free parking, over 30 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Cumberland have a kitchen?
Absolutely! We offer over 290 house rentals with a kitchen in Cumberland. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Cumberland have wifi?
Absolutely! We offer over 220 apartment 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 house rentals in Cumberland have air conditioning?
Absolutely! We offer over 230 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 1,760 vacation rentals in Falmouth, over 1,470 vacation rentals in North Deering, over 1,430 vacation rentals in Back Cove, and over 1,070 vacation rentals in Saint George.
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 guesthouse rentals in Cumberland have free parking?
Absolutely! We offer over 10 guesthouse rentals with free parking in Cumberland. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in condo rentals in Cumberland?
Experience the best of Cumberland with our condo rentals, starting at about $70 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

Apartments

Houses

Cottages

Popular amenities for Cumberland vacation rentals

Stay near Cumberland's top sights

Other great vacation rentals in Cumberland

Tiny home in Portland

Guesthouse in Harpswell

Home in Freeport

Loft in South Portland

Apartment in Portland

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 Private Suite Rentals in Cumberland?

Do house rentals in Cumberland have a kitchen?

Do apartment rentals in Cumberland have wifi?

Are there family-friendly vacation rentals in Cumberland?

Do house 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 guesthouse rentals in Cumberland have free parking?

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

Destinations to explore