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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 52 Cottages in Portland with updated reviews, rates, and availability.

Charming Cottage by the Lake❤️
Outdoor dining

Charming Cottage by the Lake❤️

9.8 out of 10, Exceptional, (11)
"My friends and I had a very lovely weekend. The cottage is well equipped, well maintained, very clean. I loved being able to bring my doggie with me. "
Charming Cottage by the Lake❤️
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!
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 Cottage w/ Covered Porch & Dock!
Miscellaneous

Lakefront Cottage w/ Covered Porch & Dock!

10.0 out of 10, Exceptional, (13)
"Small quaint cottage on lake. Very peaceful. Owner was very attentive."
Lakefront Cottage w/ Covered Porch & Dock!
Breathtaking Private, Lakefront Retreat.
Smart TV

Breathtaking Private, Lakefront Retreat.

Breathtaking Private, Lakefront Retreat.
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!
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!
Cozy Cottage On Star Lake
Fridge, microwave, oven, stovetop

Cozy Cottage On Star Lake

9.4 out of 10, Exceptional, (16)
"We truly enjoyed our stay in this lovely cottage. It was so conveniently located, clean and quiet. We were so glad to have our 30 lb. Golden doodle with us. A family of Canada geese (Mom, Dad and 3 goslings) also swam by to visit."
Cozy Cottage On Star 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
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
Lakefront Connecticut Retreat Near UConn
Fridge, microwave, stovetop, dishwasher

Lakefront Connecticut Retreat Near UConn

10.0 out of 10, Exceptional, (16)
"The house is beautiful and had everything we needed for the weekend. Since it was cooler and a bit rainy we only availed ourselves to the outside table for peaceful and quiet times. Our NYC family really enjoyed the quiet! We will be looking at this house in our future visits. "
Lakefront Connecticut Retreat Near UConn
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
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
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.
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
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!
The Answer - Charming, Unique, Tidal, Riverfront Escape - Kayaks, AC Firepit
Exterior

The Answer - Charming, Unique, Tidal, Riverfront Escape - Kayaks, AC Firepit

10.0 out of 10, Exceptional, (1)
"What a wonderful place, so peaceful.The Eight Mile River and Hamburg Cove are an authentic experience.The home is very comfortable… you will feel special!I’ll definitely return!!"
The price is AED 735
AED 1,658 total
includes taxes & fees
22 Apr - 23 Apr
The Answer - Charming, Unique, Tidal, Riverfront Escape - Kayaks, AC Firepit
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
Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Interior

Charming Windsor Home w/ Private Backyard!

3.0 star property
Charming Windsor Home w/ Private Backyard!
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, (7)
"We had a GREAT time here!! Just beautiful scenery all around. The cabin was well equipped with everything we needed essentially. I was quite impressed with how comfortable we actually were. There was a temporary power outage but it didn’t last long and management not only delivered more wood to us but also gave it to us for free as we wanted to spend our time outdoors during the outage. Im super happy to have had this experience and would absolutely be doing it again!! Thank you Postcard...
The price is AED 380
AED 585 total
includes taxes & fees
5 May - 6 May
Postcard Cabins Machimoodus
COZY Maple Tree Cabin - Situated on 6 private acres - Get Away and RELAX 😎
Exterior

COZY Maple Tree Cabin - Situated on 6 private acres - Get Away and RELAX 😎

10.0 out of 10, Exceptional, (28)
"It is certainly a cabin in the quiet woods which you would normally find in northern Vermont. We loved everything about it. My Three Sons grew up tent camping in the Yale Forest and this was that, only with a log cabin replacing Eureka tents! We loved sitting around the massive firepit and feeding the flames with plenty of seasoned, dry hardwood, cooking several meals on the coals with pie irons and steak prongs. Just loved it. "
The price is AED 1,377
AED 2,634 total
includes taxes & fees
22 Apr - 23 Apr
COZY Maple Tree Cabin - Situated on 6 private acres - Get Away and RELAX 😎
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (15)
"This is such a great property, I spent a whole month with three separate stays adjacent due to travel planning and the host was wonderful. The house is really beautiful and in a great neighborhood and it’s very comfortable and super clean. This will be a regular for me in the Hartford area. I’m looking forward to seeing what the beautiful landscaping is like in the spring and summer too."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
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.