Vacation rentals in Cumberland

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

Jo-AnnRating, 5 stars7 months ago

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

4.89 out of 5 average rating, 205 reviews

Condo in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

BrandonRating, 5 stars1 week ago

What a wonderful stay my family and I had! With two small children it was so nice to be in walking distance of so much! My wife especially took advantage of the coffee shop next door! Would recommend to family and friends and plan on booking again next year!

4.98 out of 5 average rating, 330 reviews

Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

WarrenRating, 5 stars1 month ago

Hillary's place was a wonderful place to stay for a cozy weekend getaway. It felt very homey with personal touches. We were here during a little snowstorm so we didn't spend any time outside but the yard and private deck were really nice. We had some troubles with the hot water but Hillary was very responsive and helpful! We would definitely stay here again.

4.94 out of 5 average rating, 128 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

RachaelRating, 5 stars2 days ago

Beautiful house on the pond! Perfect for our family of 4. It was comfortable and relaxing. Amy is a wonderful host! She checked in and made sure we had everything we needed. We really enjoyed our stay! Hoping to stay again sometime.

5 out of 5 average rating, 3 reviews

Home in Wells

"In Tempore" Cottage

AllisonRating, 5 stars9 months ago

Gisele and her property manager were promptly responsive. The cottage was extremely clean, newly decorated and well appointed. The layout was very comfortable for our family of four. The pools were nice and not overly crowded. The only negatives were: If not taking the trolley or golf cart, the closest pool was a half mile walk with no parking available. The further pool did have parking. Also, no outside water source/hose to rinse off. Plenty of restaurant choices nearby in Wells, Ogunquit and Kennebunkport. Wells beaches were beautiful with easy, affordable parking. Overall a wonderful stay in Wells!

5 out of 5 average rating, 6 reviews

Home in Harrison

2BR Lake House on Private Beach w/hot tub & sauna

JasonRating, 5 stars6 months ago

This is place is a gem. The lake is beautiful and the beach is very private. The house has a nice layout and is both spacious and cozy. This was our second year staying here and we plan to come back again! Dina is very responsive and great to work with.

Townhouse in Kennebunkport

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

TreenaRating, 5 stars4 months ago

I can’t say enough about this experience. The house was a great location for my mother’s 70th and Jennifer went the extra mile (literally) to make this a memorable experience for the celebration weekend. She is so easy to communicate with. Exceptional host, all the way around!

Townhouse in Old Orchard Beach

4.89 out of 5 average rating, 9 reviews

Unit 3 Getaway - Perfect for Families!

DanielleRating, 5 stars8 months ago

Perfect size for our family of 4. Location to the beach was a short walk across the street. Kitchen was modern and clean. The beds were comfortable. Pillows were available to use but we brought ours from home. Two bathrooms are always a plus with two teenage girls, only request from them was a full length mirror in the 2nd bedroom to check out their outfits. Owner reached out during our stay to check in and see if everything was going well. Very thoughtful. Would highly recommend a stay here.

Apartment in Kennebunkport

4.93 out of 5 average rating, 29 reviews

Charming Kennebunkport

EmilyRating, 5 stars7 months ago

My husband and I stayed at Kristen’s apartment for 2 weeks at the end of August and had the most amazing time! This was our 3rd time to KPT and most definitely our favorite thanks to this gorgeous Airbnb and Kristen’s hospitality. The apartment was perfect for us — was exactly as described, better than the photos with amazing windows and views, speedy WiFi perfect for working remotely. It’s a quick 4 minute drive into town, and such a beautiful area to walk around. Kristen was so responsive and helpful — there’s a super extensive list of local reccs in the apartment, and a beach pass that you can use during your stay. We loved this home away from home, and can’t wait to come back soon!

4.95 out of 5 average rating, 151 reviews

Home in Kennebunk

Quiet cozy cottage close to restaurants, beach

MikeRating, 5 stars6 months ago

Lori’s place was very cozy and a great screened in back porch. Perfect for morning coffee while taking in the scenery. Easily walkable to downtown and restaurants and right down the street from the beach. Nicely located for all things. We rented a car on our stay and travelled to Portland, Portsmouth NH and then close by towns to Kennebunk. All under an hours drive. We enjoyed our stay at Lori’s place.

Vacation rentals for every style

Get the amount of space that is right for you.

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Cumberland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Cumberland's top sights

Hannaford Supermarket280 locals recommend

Eventide Oyster Co.271 locals recommend

L.L. Bean Factory Store270 locals recommend

Peaks Island176 locals recommend

Eastern Promenade Trail251 locals recommend

Duckfat172 locals recommend

Other great vacation rentals in Cumberland

Home in Old Orchard Beach

4.88 out of 5 average rating, 25 reviews

Walk to beach, shuffleboard, and bunk room

IsaacRating, 5 stars2 months ago

The place was great! It was just as described and Nina responds very quickly and was very sweet! We had a great time!

5 out of 5 average rating, 6 reviews

Home in Harpswell

The Hideaway, In Harpswell Maine

NikkiRating, 5 stars7 months ago

We had a great long weekend at The Hideaway! The house was clean and very comfortable for 5 adults. There is a fire pit in the backyard, but plan ahead for firewood as the closest market does not sell it (we found some at Zach's Country Store in Brunswick). It's a great location with beautiful views and great restaurants nearby. We would definitely stay here again!

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars4 months ago

The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

4.75 out of 5 average rating, 20 reviews

Home in Otisfield

Log Cabin *15 acres*hunting* snowmobile*skiing

NinaRating, 5 stars3 months ago

great place for a group of friends to get away from the city ! hot tub was spacious, pool table was a great addition to the house, and the large property was awesome for exploring the woods. overall, 10/10 would definitely come back !! only downside, there were only 11 forks for 12 guests !

5 out of 5 average rating, 101 reviews

Home in Bath

Waterfront Farmhouse with Modern Flair!

Tony & KellyRating, 5 stars2 months ago

The home was very welcoming and accommodating for our family of 5. The views were spectacular at sunrise, sunset and during the snowstorm. Bald Eagles and hawks would land in the trees right in front of the house. Also, there was a skating pond down the street my family love to visit almost each evening. There was an alarm going off as soon as we arrived, Debbi was incredibly fast responding and sending someone to check it out clear it up. On the plus someone came and plowed the driveway after the snowstorm it was great. She left a basket of local food and my family ate it up. We are so thankful for our relaxing week and would love to return.

Home in Old Orchard Beach

4.98 out of 5 average rating, 89 reviews

Woods Lane Golf and Beach Vacation

MarjorieRating, 5 stars7 months ago

Our group of 5 adults were so pleased we chose to stay at Jason’s house in Old Orchard Beach. We first looked at places in Portland, but Jason’s spacious house offered a quieter setting, with parking and more amenities, at a better price. Comfortable beds, immaculate throughout. Very thoughtfully appointed, with nightstands on both sides of the beds, and superior blackout blinds in the bedrooms. And we ended up spending less time in Old Port, because we enjoyed exploring the towns south of Portland: Old Orchard Beach, Saco, Biddeford, and we found good restaurants (including Holy Donuts!) nearby. We had no issues: we contacted Jason to confirmed our arrival/departure and he responded within minutes. We highly recommend!

4.93 out of 5 average rating, 42 reviews

Cabin in Wakefield

Lakeside cabin in the woods

NicoleRating, 5 stars5 months ago

Spent Thanksgiving at the cabin and it was absolutely perfect! Jim met us upon check-in with a welcome basket full of homemade baked goods—they were delicious! Home was stocked with board games and puzzles as well. 10/10 stay.