Vacation rentals in Cumberland

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Top-rated vacation rentals in Cumberland

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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! Bonus: 2 super friendly dogs and a cat that will be around the property during your stay. New in 2024: A/C!!STHR-000718-2018

Guest favorite

Guest suite in Portland

4.95 out of 5 average rating, 114 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

Guest suite in Falmouth

4.93 out of 5 average rating, 230 reviews

Pristine Waterfront Studio Apt. Retreat

Studio apartment on the water where Casco Bay meets the Presumpscot River. Downtown Portland just 2 minutes away. Perfect opportunity to relax and enjoy the sunset and water view from the deck, head into Portland-Bon Appetite 2018 Restaurant City of the Year, drive up the coast and explore the beautiful beaches, lighthouses and quaint towns, adventure inland for amazing hikes and enjoy mountainous views. Explore Portland SeaDogs Games, events/concerts and LL Bean. Awesome music scene.

Guest favorite

Home in Freeport

4.99 out of 5 average rating, 163 reviews

"The Cozy Cottage in the heart of Freeport Village

Our cozy and tranquil one bedroom cottage is located in the heart of Freeport Village. Enjoy a short walk to restaurants, shops, and outlets – including the L.L. Bean flagship store steps away! Our clean and tastefully decorated cottage offers all you need and awaits your arrival. Wifi & Cable TV in Living Room & Bedroom. We THE COTTAGE DOES NOT ACCOMADATE CHILDREN UNDER THE AGE OF 12 FOR SAFETY REASONS. WE DO NOT ACCEPT GUESTS WITH NO REVIEWS ON AIRBNB. NO PETS DUE TO SEVERE ALLEGIES.

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, 470 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

Apartment in Portland

4.93 out of 5 average rating, 559 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.

Guest favorite

Home in Cumberland

4.95 out of 5 average rating, 280 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.

Guest favorite

Guest suite in South Portland

5.0 out of 5 average rating, 173 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer and cozy couch for lounging.

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 219 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.

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.

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

Guesthouse in Harpswell

4.95 out of 5 average rating, 431 reviews

Harpswell Studio on Waterview Property! Lobster!

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

Farm stay in North Yarmouth

4.96 out of 5 average rating, 112 reviews

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

Guest favorite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Guest favorite

Home in Yarmouth

4.92 out of 5 average rating, 486 reviews

Beautiful Coastal Maine Getaway

Guest favorite

Guest suite in Scarborough

4.98 out of 5 average rating, 139 reviews

Beautiful, private apartment!! Great location!

Guest favorite

Apartment in Gorham

4.96 out of 5 average rating, 195 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Guest favorite

Loft in Freeport

4.97 out of 5 average rating, 197 reviews

Cozy & Private Studio Apartment (Pet Friendly!)

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 Cottage Rentals in Cumberland?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with air conditioning, over 30 homes with free parking, over 30 homes with a kitchen, over 30 homes with wifi, 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 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 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.
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 1,760 vacation rentals in Falmouth, and over 1,470 vacation rentals in North Deering.
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 condo rentals in Cumberland have free parking?
Absolutely! We offer over 20 condo 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

Cottages

Houses

Popular amenities for Cumberland vacation rentals

Stay near Cumberland's top sights

Other great vacation rentals in Cumberland

Guesthouse in Harpswell

Apartment in Freeport

Farm stay in North Yarmouth

Yurt in Chebeague Island

Home in Yarmouth

Guest suite in Scarborough

Apartment in Gorham

Loft in Freeport

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 Cottage Rentals in Cumberland?

Do house rentals in Cumberland have a kitchen?

Do condo rentals in Cumberland have wifi?

Are there family-friendly vacation rentals in Cumberland?

Do cottage 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 condo rentals in Cumberland have free parking?

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

Destinations to explore