Vacation rentals in Cumberland

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Top-rated vacation rentals in Cumberland

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Guest favorite

Guesthouse in Portland

4.95 out of 5 average rating, 282 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.

Guest favorite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

Love gardens, pine trees, campfires, and birds? Curious about tiny homes? Our 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping the beverage of your choice from your private deck. It will be a unique and amazing experience and one you will remember! It has heat, A/C, and fans. Bonus: 2 friendly dogs and a cat that will be around the property during your stay. STHR-000718-2018

Guest favorite

Guest suite in Freeport

4.96 out of 5 average rating, 187 reviews

Waterfront Private Apartment only 5 min to LL Bean

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 7.5 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

Guest favorite

Yurt in Cumberland

4.94 out of 5 average rating, 155 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. -New spring 2024 an outdoor solar shower- Water for the outdoor shower and outdoor sink is seasonal 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.

Guest favorite

Apartment in Yarmouth

4.94 out of 5 average rating, 100 reviews

Quiet and Private Apartment

Discover the greater Portland area and unwind in our cozy 2-bedroom apartment, an ideal retreat for visitors exploring Maine. Just a 20-minute drive from Portland, 10 minutes from a public beach, and 15 minutes from LLBean. Please note: Our kitchenette is equipped for quick bites and light meals, with a mini-fridge, toaster oven, electric fry pan, and microwave. While perfect for whipping up a quick breakfast or lunch, it's not suited for full-scale culinary endeavors. No pets please.

Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 115 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!

Guest favorite

Loft in Freeport

4.97 out of 5 average rating, 198 reviews

Cozy & Private Studio Apartment (Pet Friendly!)

Recently renovated studio apartment, very cozy, with a private side yard and entrance, kitchenette and TV (Roku with 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!

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

Guest favorite

Cabin in Freeport

4.98 out of 5 average rating, 473 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

Guest favorite

Home in Freeport

4.85 out of 5 average rating, 249 reviews

Home On Pond in Woods - Guest Suite

Private ground-level apartment at 11 Fox Hill Rd, near downtown Freeport but in the woods, with access to great swimming pond and trails, with winter ice hockey, ice skating, and XC skiing at the property. Separate BR has full daylight sliding glass doors. Sleeper-sofa (or available air mattress) are in main part of semi-finished but pleasant basement. Private bathroom and entry/exit. Freeport Registration # STRR 2023-42

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 222 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.

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 152 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.

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

Guest suite in Falmouth

4.93 out of 5 average rating, 230 reviews

Pristine Waterfront Studio Apt. Retreat

Guest favorite

Farm stay in North Yarmouth

4.96 out of 5 average rating, 113 reviews

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

Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 196 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Guest favorite

Loft in South Portland

5.0 out of 5 average rating, 110 reviews

Serene studio apartment, close to everything.

Guest favorite

Home in Lisbon

4.94 out of 5 average rating, 337 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Guest favorite

Guest suite in Portland

4.91 out of 5 average rating, 201 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

Guest favorite

Apartment in Freeport

4.91 out of 5 average rating, 195 reviews

1000 sq. ft. 1BR+ Apt Close to Town & Nature

Guest favorite

Guest suite in Scarborough

4.98 out of 5 average rating, 139 reviews

Beautiful, private apartment!! Great location!

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 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 cottage rentals in Cumberland have wifi?
Absolutely! We offer over 30 cottage 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 cottage rentals in Cumberland have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Cumberland. Enjoy a tailored experience with all the comforts you desire.
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 apartment rentals in Cumberland have free parking?
Absolutely! We offer over 160 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 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.
Are there Cumberland vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Cumberland, available on Airbnb. Make a splash and soak up the sun in style!

Vacation rentals in Cumberland

Top-rated vacation rentals in Cumberland

Vacation rentals for every style

Apartments

Cottages

Houses

Popular amenities for Cumberland vacation rentals

Stay near Cumberland's top sights

Other great vacation rentals in Cumberland

Guest suite in Falmouth

Farm stay in North Yarmouth

Apartment in Gorham

Loft in South Portland

Home in Lisbon

Guest suite in Portland

Apartment in Freeport

Guest suite in Scarborough

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 house rentals in Cumberland have a kitchen?

Do cottage rentals in Cumberland have wifi?

Are there family-friendly vacation rentals in Cumberland?

Do cottage rentals in Cumberland have air conditioning?

Are there pet-friendly vacation rentals in Cumberland?

Are there vacation rentals with a dedicated workspace in Cumberland?

Do apartment rentals in Cumberland have free parking?

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

Are there Cumberland vacation rentals on Airbnb with pools?

Destinations to explore