
Cottage vacation rentals in Cumberland
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Top-rated cottage rentals in Cumberland
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Popular amenities for Cumberland cottage rentals
Cottage rentals with a hot tub

Cozy Cottage close to Beach, Pool and more!
Dear Tim and Kimberly - I wanted to express how much we enjoyed our stay at your delightful two-bedroom cottage. The accommodations were not only beautifully furnished but also incredibly comfortable. The added amenities, including the pool, hot tub, and gym, made our stay even more enjoyable, offering plenty of options for relaxation and fitness. We also loved how close the cottage was to the local restaurants and the beach—it was the perfect location for a relaxing getaway. Your attention to detail made all the difference, and we couldn't have asked for a better experience. I will definitely recommend your place to others and look forward to returning in the future! Janelle Q PS - I live in Florida and upon my return from Maine, am being greeted by Helene. JQ

Make this family-friendly cottage your summer spot
Jessica was very communicative and her place was in a great location to access the area’s attractions. A comfortable home away from home. We enjoyed the pool and wish we had stayed longer. Thank you!

Maine Lakehouse, 3 Bedrooms, 2 baths, waterfront
Nice private area, close by to a few small-towns for groceries, gas, etc. Property was very scenic and often only sounds that could be heard were birds. Slept 5 comfortably and never felt crowded. 10/10

Cozy beach cottage with pool & hot tub
Lovely one night stay at this sweet little cottage! Grounds are well-kept, enjoyed morning coffee on the front porch. AC kept it nice and cool. Convenient location close to a great donut shop- Congdon’s and our favorite ice scream spot- Scoop Deck. Chloe is a gracious host and even granted us a late check-out!

Lakeside Cozy Cottage in Nature | Hot Tub
This trip was more than we could've ever wanted! The property was lovely and the hosts were more than accommodating and made sure everything was as comfortable as it could've been! I'd recommend anyone to book with these hosts and I will definitely be booking again!

Fully Renovated/4min to K-port/HotTub/Game Room
We had a great stay at Audrey & Seb's place. It was spacious, beautifully decorated, and extremely clean. The beds were super comfortable, the location was private and close to town, and there was so much thought put into all the little details. What an absolutely wonderful place. Thank you so much!

Beautifully renovated 2-bedroom cottage
Everything was so perfect !! thank you for hosting us !!

Contemporary Cottage With Ocean View 13
Terrific stay! The cottage was modern, clean, convenient and lovely. The pools are great for kids, and the cottage is near to restaurants, beaches etc. Great place for a holiday.
Pet-friendly cottage rentals

Lovely cottage on Sunrise Lake, Middleton, NH.
Another wonderfully relaxing stay! We really enjoyed the new screened in porch for morning coffee, late afternoon snacks, and evening games. The rainy days were just as lovely as the beautiful ones. We enjoyed the cozy gas stove on the cooler days, and we just couldn't have been more delighted by the welcome note and gift upon our arrival.

Cottage on Todd Bay
Our group of 4 had a wonderful stay here. It had everything we needed and John was extremely helpful. We cooked several meals and visited nearby attractions.

Osprey Cottage, peaceful setting, walk to beach
Elizabeth was a wonderful host and her home is perfect for a peaceful, relaxing vacation. The house was spotless, well appointed, and very cozy. The short walk to the beach and town market is really convenient. Her rental is a perfect home base if you’re visiting Portland or exploring the Maine coast nearby.

Pet Friendly Audubon Bring Your Fishing Gear!
What an amazing setting! Right on the water. We saw seals, osprey, and, we think, an eagle.Also the most beautiful sunrise. The house is cozy and comfortable and really really clean. We found everything we needed and some thoughtful extras. Tamara is an excellent host!

Sunset Haven - Little Sebago Lake
Absolutely loved our stay at this lake cabin! It's nestled right on the water, making it a perfect spot for peaceful mornings and unbeatable fishing. The sunsets over the lake are absolutely stunning — a real highlight of the trip. The cabin itself has a rustic charm, filled with unique vintage touches that make it feel cozy and full of character. It's quiet, far enough from the city to truly relax, but still conveniently close to town if you need anything. A wonderful place to unwind and make lasting memories with family. Can't wait to come back!

Waterscape Cottage - private waterfront
We had a wonderful time at Ann’s. The cabin was great and exactly as described, clean and very comfortable. The property is amazing with lots of privacy and in a great location to explore the Maine coast during the day. Don’t miss hiking down to the trestle bridge to see the herons. Ann thought of everything to make sure we would be comfortable during our stay and she was happy to offer suggestions on places to go and things to see.

Rustic Pebble Cottage in beautiful Bridgton, Maine
Pebble Cottage was so peaceful yet close to everything. We kept ourselves quite busy locally and Cheryl's place was a perfect spot to unwind and relax at the end of a busy day. The host is a beautiful artist and an exceptional, sweet human being. We hope to return in the Fall. Thanks Cheryl!

Cozy Cottage on Highland Lake
Perfect little Maine cabin getaway! We enjoyed our stay so much. The cabin was clean, easy to find, and had everything we needed for four people and two dogs. Cannot recommend enough!
Private cottage rentals

Tranquil waterfront cottage
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.

Cheerful 1 Bedroom Cottage Steps From The Ocean
Wonderful place clean and very cozy house I indicate

Custom Built Quaint Knotty Pine Cottage
We felt truly comfortable and at home in the Knotty Pine Cottage. We spent 19 days there! My husband was working again in the area and the job site was 5 minutes away. On his days off we took advantage of hiking the numerous Boothbay Region Land Trust properties. We highly recommend Porter Preserve, Oven's Mouth Preserve and Oak Point Farm. We loved walking around beautiful Ocean Point and an afternoon on Popham Beach. We also spent an afternoon reading our books at Barrett's Park. The house is well stocked with everything you'll need to prepare meals and there is a Hannaford Grocery store 10 minutes away. We recommend The Thistle Inn in Boothbay Harbor if you enjoy crabcakes that are made from scratch. We're looking forward to our next trip back to Southport and hope the cottage will be available. Many many thanks to our responsive hosts! They made us feel welcome and comfortable in their home!!

Seaside Escape
The location was amazing. Just a few steps to Crescent Beach. I actually took my coffee down there and watched the sunrise in the morning. So beautiful. The cottage was clean and comfortable. Kristin was very responsive and helpful. Don't miss out on the clam chowder at the Lobster Pound less than 100 meters away. We'd definitely come again.

Waterfront Cricket Cottage Pleasant Pond Turner ME
We had a wonderful and peaceful stay at the cottage. The location was perfect for a relaxing getaway surrounded by nature and offering stunning sunset views of the pond along with kayaks to go out and enjoy! The cottage itself was cozy and clean and we felt at home! Darlene was welcoming and attentive ensuring everything was just right for our stay! I highly recommend this charming retreat for anyone looking for a peaceful stay! It was a bit chilly so we were able to enjoy the fire pit outdoors with the wood that was provided! I can’t wait to return and stay longer! We can clearly see why this cottage has so many positive reviews!!

Saco Cozy Cottage! Minutes From Old Orchard Beach
The cottage was perfect for our needs and had everything! Auria was extremely helpful and responded to us quickly! I would definitely stay there again!

OGUNQUIT Walk to Beach and Town, Renovated Cottage
Would absolutely recommend this quaint little home! The place was clean and as described, and Lisa was very responsive and helpful. This is located right in the middle of town, a few minutes walk to Perkin’s Cove and equally as close to the beach.

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike
I really enjoyed my stay here. It was so quiet and peaceful. Vianna was responsive and even left us a little treat which made the stay all the better. very clean and the kitchen had everything! some spices, coffee, creamer etc.. highly recommend for a quiet getaway.
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- Wells Beach
- Cranmore Mountain Resort
- Ogunquit Playhouse
- East End Beach
- Long Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Long Sands Beach
- Popham Beach State Park
- Purity Spring Resort
- Mt. Abram
- King Pine Ski Area
- Diana's Baths
- Parsons Beach
- Portland Museum of Art
- Mothers Beach
- Ferry Beach
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Cliff House Beach
- Dunegrass Golf Club
- Palace Playland
- Funtown Splashtown USA