Family-friendly vacation rentals in Cumberland

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Top-rated family-friendly rentals in Cumberland

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favourite

Guest suite in New Gloucester

4.98 out of 5 average rating, 173 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

May 4 – 9

$189 CAD per night

Guest favourite

Apartment in Falmouth

4.96 out of 5 average rating, 137 reviews

Falmouth Waterfront Carriage House Apt

Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

Oct. 1 – 8

$451 CAD per night

Guest favourite

Guesthouse in Harpswell

4.95 out of 5 average rating, 431 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

May 9 – 16

$200 CAD per night

Guest favourite

Tiny homes 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

Sep. 19 – 26

$228 CAD per night

Guest favourite

Home in Gorham

4.99 out of 5 average rating, 138 reviews

Beautiful Home In Gorham Maine

Well appointed, bright and sunny apartment for two people in a quiet neighborhood. Large private back yard, formal gardens and pond, elevated deck, well stocked kitchen. 25 mins. to downtown Portland and the seacoast area. Minutes to local nature trails, swimming, kayaking, dining, supermarket & bakeries. ** NO PROFILE/REVIEWS? please provide a little info about whose coming, ie, name/age/occupation, reason of visit, etc, and any other info you wish to provide. Thank you!

Jan. 9 – 16

$282 CAD per night

Guest favourite

Apartment in Lisbon falls

4.95 out of 5 average rating, 383 reviews

Charming Victorian farmhouse 1880's bedrooms-2

Victorian farmhouse 1880's Stay in an "era gone by". Private 2 bedroom. Original hardwood floors. Original pocket doors. Sleeps 6. Has living room, kitchen, dinning area 1 bathroom with tub , study area. Charming town, population 4000+. smoke free house. Private keyless entry. The blue door. Free wifi, cable, roku. Has keurig coffee maker with free coffee, dishes, pots, pans, silverware, nu-wave cooktop, toaster, microwave, fridge, pack n play. Queen beds. W & D private.

Apr. 27 – May 4

$168 CAD per night

Superhost

Apartment in Portland

4.78 out of 5 average rating, 304 reviews

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

Nov. 12 – 19

$180 CAD per night

Guest favourite

Cottage in Portland

4.9 out of 5 average rating, 492 reviews

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet Portland neighborhood only a 7-10 minute drive (and $9 Uber ride) from downtown Portland, the Old Port, and all local visitor attractions. The cottage is a mile down the road from the Allagash Brewing complex and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

Aug. 17 – 24

$264 CAD per night

Guest favourite

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.

May 22 – 29

$291 CAD per night

Guest favourite

Apartment in Freeport

4.91 out of 5 average rating, 195 reviews

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

This very spacious and light filled apartment has beautiful views of a marsh and the headwaters of the Harraseeket River. It is also across the street from a 100+ acre bird sanctuary. There is a queen bed in the bedroom, a twin in the large living room, and a twin in a small nook under the eaves off of the kitchen. You can put kayaks in across the street and it is a short 20 minute walk into downtown Freeport. Great year-round location.

Jan. 21 – 28

$181 CAD per night

Guest favourite

Farm stay in Gray

4.94 out of 5 average rating, 249 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!

Jan. 22 – 29

$235 CAD per night

Guest favourite

Home in Yarmouth

4.92 out of 5 average rating, 486 reviews

Beautiful Coastal Maine Getaway

Set back among backdrop of tall pines on Maine's coast is our immaculately clean, and very private 4 bedroom, 2 bath home in Yarmouth. Quiet and secluded, and perfectly located between Portland and Freeport, it's an amazing place to decompress with family and friends. Our home comes complete with absolutely everything you need to enjoy your stay!

Nov. 12 – 19

$589 CAD per night