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Check prices for these dates

Next weekend
7 Mar - 9 Mar
In two weeks
14 Mar - 16 Mar
In one month
28 Mar - 30 Mar
In two months
25 Apr - 27 Apr

Compare 42 Cottages in Portland with updated reviews, rates, and availability.

Charming Cottage by the Lake❤️
Outdoor dining

Charming Cottage by the Lake❤️

9.6 out of 10, Exceptional, (8)
"Very cozy little home. "
Charming Cottage by the Lake❤️
Go Jump in the Lake!

Go Jump in the Lake!

10.0 out of 10, Exceptional, (138)
"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "
Go Jump in the Lake!
Updated cottage "Beriozka" on Cedar Lake
Exterior

Updated cottage "Beriozka" on Cedar Lake

10.0 out of 10, Exceptional, (5)
"The cottage was adorable and perfectly suited our needs as a friend getaway. When I got Covid in August (our original vacation date), the host was so understanding and allowed us to move the time. Chester was a great town, beautiful scenery, and yummy restaurants. Would stay here again!"
Updated cottage "Beriozka" on Cedar Lake
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Fridge, microwave, oven, stovetop

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Fridge, microwave, stovetop, cookware/dishes/utensils

Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!

9.4 out of 10, Exceptional, (23)
"We thoroughly enjoyed our stay. This cottage perfect for two people. The location has all the amenities you could ask for. Climbing up and down the 43 steps to cottage can be tiring especially for the elderly. There is Liquer store very close buy and grocery store within 5 miles. I must say that prices there very high, but in no way does that reflect on owner. We certainly are looking forward to coming back for another stay."
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Lakefront Cottage w/ Covered Porch & Dock!
Interior

Lakefront Cottage w/ Covered Porch & Dock!

3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Relax with a beautiful lake view
Outdoor dining

Relax with a beautiful lake view

10.0 out of 10, Exceptional, (19)
"Great location"
Relax with a beautiful lake view
Lakefront Connecticut Retreat Near UConn
Fridge, microwave, stovetop, dishwasher

Lakefront Connecticut Retreat Near UConn

10.0 out of 10, Exceptional, (14)
"We stayed for 2 nights while my daughter was swimming at UCONN. Place was clean and warm and had everything we could need. Short drive to campus and beautiful views of the frozen lake!"
Lakefront Connecticut Retreat Near UConn
Family Friendly Waterfront Cottage
Private kitchen

Family Friendly Waterfront Cottage

4.0 out of 10, (1)
"This property is completely misrepresented! I sent pictures in an email to someone named Luis two days ago. 1. Home is on a gravel road and you need to walk down a steep hill to get to the house. 2. House is covered in cob webs inside and out and windows are dirty and covered in green mold. 3. Two queen beds listed turned out to be full size mattresses (we measured!) so that my husband and I had to sleep in separate rooms. 4. Third bedroom had a sleeper sofa that we had to use to keep an...
Family Friendly Waterfront Cottage
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Miscellaneous

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Cozy 3 bd Cottage w/ access to private lake
Private kitchen

Cozy 3 bd Cottage w/ access to private lake

10.0 out of 10, Exceptional, (2)
"Beautiful place and excellent house."
Cozy 3 bd Cottage w/ access to private lake
Reel Simple on Bolton Lake
Outdoor dining

Reel Simple on Bolton Lake

2.0 star property
9.8 out of 10, Exceptional, (22)
"We were a little nervous upon arrival, it was exceptionally cold that day Dec 22nd, 2 deg at night ,and we were afraid it wouldn't heat up. However, between the heat pumps and the electric fireplace, it became toasty! Very convenient, 2 bathrooms great !We would definitely book again !"
Reel Simple on Bolton Lake
Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.
Shower, hair dryer, towels, soap

Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.

2.0 star property
9.4 out of 10, Exceptional, (3)
"Our stay was super easy. Not a far walk to the beach. Communication was super fast and easy as well! Only a slight musty smell in the big bedroom, but not enough for me to take off any stars. "
Escape to Caladan Cottage! Cozy pet-friendly lake house: AC, multi-beach access.
Modern Terryville Cottage w/ Deck & Lake View!
Fridge, microwave, stovetop, dishwasher

Modern Terryville Cottage w/ Deck & Lake View!

9.0 out of 10, Wonderful, (4)
"This cottage was just as the pics show. Great communication with host prior to visit as well as a "Thank you" This is the perfect spot to relax & recharge from stress. The cottage wraps you in warmth, and charm."
Modern Terryville Cottage w/ Deck & Lake View!
Lake Getaway at Coventry Lake! close to Uconn
Exterior

Lake Getaway at Coventry Lake! close to Uconn

10.0 out of 10, Exceptional, (17)
"This cottage is adorable-beautifully decorated and well appointed. I seriously want to hire whoever decorated this house for my house! Excellent communication with the owner. We stayed in January and it was cold!! The gas logs made it nice and toasty, but it took us a while to figure them out, written instructions on how to turn on the fireplace would have been helpful-but other than that we had a great stay! "
Lake Getaway at Coventry Lake! close to Uconn
Wolcott Home w/ Deck: Near Connecticut Attractions
Interior

Wolcott Home w/ Deck: Near Connecticut Attractions

3.0 star property
Wolcott Home w/ Deck: Near Connecticut Attractions
The perfect New England getaway only a 10 minute walk to downtown!
Exterior

The perfect New England getaway only a 10 minute walk to downtown!

10.0 out of 10, Exceptional, (4)
"Beautifully updated home inside and out! Well stocked and very clean! The gas fireplace was definitely a plus! Location was perfect for a walk into town, or to get in the car and hop on the highway to go exploring. Owners were super accommodating and easy to work with as well."
The perfect New England getaway only a 10 minute walk to downtown!
Spacious Lake Hayward Cottage
Miscellaneous

Spacious Lake Hayward Cottage

10.0 out of 10, Exceptional, (5)
"We enjoyed our stay in this new home. Attractive and comfortable- we were very pleased with everything the property offered. No detail was overlooked- the kitchen was well supplied, and the spacious upstairs bedroom/extra living space and master bedroom were perfect for our family. Pretty lake views were an added bonus. Thank you, Nick, for a great visit!"
Spacious Lake Hayward Cottage
Historic Essex Home w/ Large Yard Near Downtown!
TV

Historic Essex Home w/ Large Yard Near Downtown!

3.0 star property
Historic Essex Home w/ Large Yard Near Downtown!
Charming 2-bedroom farm cottage in quiet Killingworth neighborhood
Miscellaneous

Charming 2-bedroom farm cottage in quiet Killingworth neighborhood

Charming 2-bedroom farm cottage in quiet Killingworth neighborhood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Portland

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
The price is AED 496
AED 570 total
includes taxes & fees
18 Mar - 19 Mar
Postcard Cabins Machimoodus
Luxe Lake House in Connecticut
Fridge, microwave, oven, stovetop

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (2)
"The house easily accommodated my friends and family for a weekend of relaxation. The place is very spacious with all modern amenities. We especially loved waking up to the gorgeous view of the lake in the back. The views were breathtaking. Would definitely consider going back. "
The price is AED 1,288
AED 3,321 total
includes taxes & fees
18 Mar - 19 Mar
Luxe Lake House in Connecticut
Amazing Lakefront Property
Dining

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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