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Holiday rentals in Cumberland

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Quick stats about holiday rentals in Cumberland

  • Total holiday rentals

    Explore 170 holiday rentals in Cumberland

  • Nightly prices starting at

    Cumberland holiday rentals start at €52 per night before taxes and fees

  • Verified guest reviews

    Over 7,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wifi availability

    170 of Cumberland holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cumberland rentals

  • 4.9 Average rating

    Cumberland stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated holiday rentals in Cumberland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cottage in Yarmouth

Buoys on Bates | Couples' Cottage near Portland

Buoys on Bates is a newly renovated, contemporary cottage 15 minutes from Portland and moments from Yarmouth's historic Main Street. Step into a spotless, light filled space with a full kitchen, fast 350 Mbps wifi, premium Tuft & Needle queen bed, in-unit washer/dryer, efficient A/C, and Level 2 EV charger right at the door. Walk to shops, restaurants, and the Royal River, then set out for Portland, Freeport, beaches, and breweries. Buoys on Bates is your easy, comfortable base for all of Maine.

4.96 out of 5 average rating, 179 reviews
Top guest favourite
A modern two-story home is set against a backdrop of trees showcasing autumn foliage. The house features a combination of wood and siding, with a covered front porch and two chairs. A paved driveway leads to the two-car garage, enhancing accessibility.
Home in Cumberland

Tranquil Home on Nature Preserve

Beautiful modern home with large windows & ample natural light. Located in a tranquil neighborhood on a nature preserve. Each of the 3 bedrooms is equipped with a smart TV, heat pumps/ac units, high speed Wi-Fi, & all the amenities to ensure your comfort. Enjoy high end appliances, propane fireplace, luxury hot tub, back patio & fire pit. Conveniently located in Cumberland with easy access to I95, Portland, Sebago Lake, &Coastal Maine. Trail access to Knight’s Pond Preserve along property.

4.98 out of 5 average rating, 63 reviews
Top guest favourite
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in Portland

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

4.97 out of 5 average rating, 174 reviews
Top guest favourite
The modern chalet is framed by lush greenery, presenting a welcoming entrance. The large windows offer views of the water in the distance, while the surrounding landscape features a blend of trees and shrubs. The well-maintained exterior reflects a serene, natural setting.
Home in Cumberland

Water views, privacy, decks, minutes to Portland

Wake up to coffee and breakfast on the deck watching eagles and other native birds of Maine then walk the private botanical garden. This is an deal location for a Maine getaway. This modern chalet sits on 4 private acres 15 minutes to Portland on the Cumberland Foreside. Enjoy panoramic water views, expansive decks with tons of outdoors seating, 2 minutes from the marina, town landing beach, 5 minutes to Sandy Beach, walk to mountain biking & hiking trails. Open concept perfect for relaxation.

4.99 out of 5 average rating, 103 reviews
Top guest favourite
A relaxed living area features a mix of seating options, including a patterned armchair and a leather sofa. A wooden coffee table sits in the center. Natural light enters through two windows, illuminating potted plants and wall art that enhances the tranquil setting.
Flat in Yarmouth

Sweet 1-Bedroom Apartment in Vintage Village Cape

Built roughly 200 years ago, the traditional cape housing this first-floor apartment is located on a hilltop above the Royal River, just steps from restaurants, trails, and waterfront. It's been thoroughly renovated, and features pretty much all the comforts of home—including a full kitchen with dishwasher, a wood-burning fireplace insert, an all-natural mattress (super comfy), and a clawfoot tub-equipped bathroom. Oh, and if you're bringing a third, let me know—and I'll roll in the rollaway.

4.97 out of 5 average rating, 192 reviews
Top guest favourite
A serene waterfront scene captures calm waters dotted with boats gently bobbing in the harbor. Rocky shores lead to lush greenery in the background, with a clear blue sky above, creating an inviting coastal atmosphere in this Maine setting.
Flat in Falmouth

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.

4.96 out of 5 average rating, 198 reviews
Top guest favourite
A cozy bedroom features rustic wooden paneling and a sloped ceiling. A spacious bed with red and white bedding sits next to a wooden nightstand with a lamp. Additional storage baskets are arranged nearby, and light filters in through a window decorated with a sheer curtain.
Home in Cumberland

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 group of 6 or a couple of 2 to unwind.

4.96 out of 5 average rating, 338 reviews
Guest favourite
A modern kitchen with bright cabinetry features a central wooden table set for four. A simple vase with white flowers sits at the center. Light is seen coming through a nearby window, highlighting the retro blue refrigerator and clean countertops.
Home in Yarmouth

Close to Breweries, Outlets, and Portland Food!

Newly renovated and centrally located in charming Yarmouth Village! Enjoy a short walk to shops and restaurants, drive 15 minutes to Portland Old Port and renowned restaurants, or 5 minutes to Freeport Breweries/Outlets. Maine Beer Company, Mast Landing, LL Bean, Ottos, Royal River Grill all just minutes away. This is the perfect pit stop on your way to Acadia/ski mountains or to plan a day trip up the coast to Boothbay Harbor.

4.96 out of 5 average rating, 146 reviews
Guest favourite
A sunlit sunroom features three woven chairs adorned with soft cushions in varying shades of blue. A low wooden table with a vintage checkers board is situated in the center. Sheer white curtains gently drape around the windows, allowing natural light to enter.
Home in Falmouth

Beautiful +Nostalgic + Coastal Maine Cottage

Conveniently located 15 minutes from Portland Jetport and 10 minutes from Old Port in downtown Portland, this renovated 1850's, charming, and sunny historic home is perfect for your Maine getaway. It is a fantastic home-base for exploring Southern and Midcoast Maine while enjoying close proximity to Portland's award-winning restaurants and attractions as well as beautiful beaches, islands, museums, lighthouses, and much more.

4.85 out of 5 average rating, 230 reviews
Top guest favourite
Guest house in Yarmouth

Charming Guest House: Accessible

Charming guest house with a private entrance, modern kitchen, and cozy living space. Accessible features include an elevator and curbless showers for easy mobility. Relax in the garden or explore nearby attractions like Freeport Outlets, L.L. Bean and Portland. Perfect for families, couples, or guests with accessibility needs, offering a peaceful retreat with easy access to shopping, dining, and outdoor activities

5.0 out of 5 average rating, 19 reviews
Top guest favourite
A light-filled studio interior showcases a sitting area with a patterned sofa and wooden chairs, complemented by a dresser and small table. A fully equipped kitchen is visible, featuring a refrigerator and minimalist decor. Natural light enters through two windows, creating a serene ambiance.
Guest house in Cumberland

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.

4.95 out of 5 average rating, 308 reviews
Guest favourite
The exterior of a historic farmhouse is presented, featuring two stories with white trim around multiple windows. A central front door is flanked by light fixtures, and landscaped greenery, including hostas, surrounds the entrance. A well-maintained lawn adds to the inviting aspect of the property.
Home in Falmouth

Wild Rose Farm -Three Queen Suites

Wild Rose Farm is a historic, antique farmhouse in a suburban setting close to Route 1 in Falmouth. The main house has 3 queen suites with additional beds as needed. This farmhouse is perfect for a family or friend getaway. This listing is for the whole farmhouse + barn. Small events may be allowed with prior approval. Please inquire FMI

4.91 out of 5 average rating, 104 reviews

Popular amenities for Cumberland holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Cumberland's top sights

Royal River Park

15 locals recommend

Falmouth Town Landing

14 locals recommend

Yarmouth Farmers Market

5 locals recommend

Presumpscot Falls

4 locals recommend

Sunflower Farm Creamery

4 locals recommend

Falmouth Memorial Library

3 locals recommend

Other great holiday rentals in Cumberland

Guest favourite
A wooden dock extends over calm waters, surrounded by lush greenery and trees. The clear sky, dotted with white clouds, provides a serene backdrop. The gentle slope of the landscape leads to the water's edge, emphasizing the peaceful nature of the setting.
Island in Cumberland

Island Cottage Getaway in Casco Bay!!

4.9 out of 5 average rating, 88 reviews
Top guest favourite
The exterior of the townhouse is shown, featuring a light grey facade, a welcoming farmers porch with red chairs, and a landscaped front yard. Lush greenery and stone borders enhance the curb appeal, while the driveway leads toward the entrance.
Flat in Yarmouth

The Inn on Bridge Street

4.98 out of 5 average rating, 80 reviews
Top guest favourite
A circular fire pit is surrounded by several black Adirondack chairs, set on a lush green lawn. The tranquil surface of the lake reflects the blue sky and fluffy clouds, while trees in varying shades of green line the opposite shore.
Home in Windham

Lakefront | Dock + Fire Pit Near Sebago & Portland

4.97 out of 5 average rating, 38 reviews
Top guest favourite
A dining area features a large blue table accompanied by a long bench and two chairs, creating inviting seating. Natural light filters in through two windows adorned with sheer curtains, illuminating the warm wood flooring and accentuating the room's cozy ambiance.
Flat in Yarmouth

Peaceful 2nd floor apt in Yarmouth Village

4.93 out of 5 average rating, 75 reviews
Top guest favourite
An outdoor patio area features a circular fire pit surrounded by six blue Adirondack chairs. A stack of firewood is neatly arranged beside the fire pit. Lush greenery and flowering plants enhance the space, creating an inviting atmosphere for gatherings.
Flat in Yarmouth

Midcentury Modern 2 Bedroom Village Oasis

5.0 out of 5 average rating, 53 reviews
Top guest favourite
Home in Freeport

Mermaid's Chair | Private Beach | Hot Tub

5.0 out of 5 average rating, 16 reviews
Top guest favourite
A spacious backyard features a firepit surrounded by six blue Adirondack chairs, creating a cozy gathering area. The well-maintained lawn is bordered by trees, and the home is visible in the background with warm lighting illuminating its deck and windows.
Home in Windham

Maine Vacation Home on the Water

5.0 out of 5 average rating, 66 reviews
Guest favourite
A single-story house features a gray-shingled exterior with a red roof and front steps leading to a central door. Surrounding landscaping includes neatly trimmed shrubs and vibrant flowers. A gravel driveway provides access to the home, complemented by a lawn area and a few trees in the background.
Home in Falmouth

Charming Coastal Home

4.96 out of 5 average rating, 51 reviews

When is the best time to visit Cumberland?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price€186€177€169€198€199€215€225€222€198€208€211€194
Avg. temp-6°C-4°C1°C6°C12°C18°C21°C20°C16°C10°C4°C-2°C

Frequently Asked Questions

  • Are there family-friendly vacation rentals in Cumberland?

    Cumberland has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Cumberland?

    Experience the best of Cumberland with our house 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.

  • Are there pet-friendly vacation rentals in Cumberland?

    Four-legged friends are welcome in Cumberland. Choose from more than 50 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 90 vacation rentals in Cumberland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Cumberland house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Cumberland, available on Airbnb. Make a splash and soak up the sun in style!

  • Do apartment rentals in Cumberland have air conditioning?

    Absolutely! We offer over 20 apartment rentals with air conditioning in Cumberland. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Cumberland have a kitchen?

    Absolutely! We offer over 20 apartment 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 100 house rentals with wifi in Cumberland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cumberland have free parking?

    Absolutely! We offer over 100 house rentals with free parking in Cumberland. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Cumberland?

    Enhance your stay in our House Rentals with the most popular amenities: over 80 homes with air conditioning, over 100 homes with wifi, over 100 homes with free parking, over 90 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore