Photo by Rick Bucchino

Book a Portland Cottage

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Cottages in Portland

Charming Deep River Vacation Rental on Star Lake!
7.0 out of 10, Good, (4)
"Nice relaxing small house for a quick weekend getaway. Plenty of space in the kitchen and bedrooms. The shower is very very small, especially with a curtain that you kind of have to hold back away from you while you shower. If you like very firm beds youre in luck, the matresses are pretty firm. I would bring your own pillows as those provided were very thin. Other than that, its the perfect spot for a getaway. We had a wonderful relaxing weekend."
Charming Deep River Vacation Rental on Star Lake!
Lakefront Connecticut Retreat Near UConn
10.0 out of 10, Exceptional, (13)
"Amazing place and view. Entire stay was great to share while in for family weekend. Very welcoming and hospitality. 10!"
Lakefront Connecticut Retreat Near UConn
Charming Cottage by the Lake♥️
9.8 out of 10, Exceptional, (6)
"Clean, all the amenities and a great host. We will stay here again!! ❤️❤️❤️"
Charming Cottage by the Lake♥️
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!
3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
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!
Go Jump in the Lake!
10.0 out of 10, Exceptional, (137)
"We like this place a lot. House was clean and Todd was very responsive to my questions. There are two bedrooms with one on the second floor. One thing we didn’t realize was, to get to the second floor there is a spiral staircase. "
Go Jump in the Lake!
The Little Red Cottage
10.0 out of 10, Exceptional, (4)
"This place was so cute! The pictures don't do it justice. The layout of the house is perfect. The rooms are spread out so your not on top of each other with larger groups. Each room has an a/c which was so nice. This house is in a great location, in such privacy, but so close to stores, food, and shops. Will definitely be back. Thanks so much Jodi for being so communicative and opening your doors to my family and I. See ya soon!!!"
The price is NZ$632
includes taxes & fees
2 Dec - 3 Dec
The Little Red Cottage
Relax with a beautiful lake view
10.0 out of 10, Exceptional, (19)
"Great location"
Relax with a beautiful lake view
Lake Getaway at Coventry Lake! close to Uconn
10.0 out of 10, Exceptional, (13)
"We absolutely loved this property. The furnishings were perfect, the beds and pillows were comfy and I especially loved sitting on the porch watching the neighborhood buzz around. I will be back!"
Lake Getaway at Coventry Lake! close to Uconn
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!
Wolcott Home w/ Deck: Near Connecticut Attractions
3.0 star property
Wolcott Home w/ Deck: Near Connecticut Attractions
Updated cottage "Beriozka" on Cedar Lake
10.0 out of 10, Exceptional, (3)
"Vert cozy and quiet"
Updated cottage "Beriozka" on Cedar Lake
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
10.0 out of 10, Exceptional, (2)
"A perfect stay - John and his family were truly wonderful. The house is attached to thier main house, but also very private and secure. We were in town for a wedding weekend and this was the perfect spot for us - truly a beatuiful property! John was helpful in telling us about all of the local spot and supplying us with everything we needed. His wife even welcomed us with a cheese board and wine! Thanks John and family - we had a great time!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
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.
Breathtaking Private, Lakefront Retreat.
Lakefront Home, Close to Mt Southington!
3.0 star property
Lakefront Home, Close to Mt Southington!
Pet-friendly Lebanon House w/ Lake Access!
3.0 star property
Pet-friendly Lebanon House w/ Lake Access!
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
Charming Farmhouse w/ Pool & Fishing Pond!
3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!
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.
Don't see what you're looking for?
See all available properties in Portland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Portland

Historic Essex Home w/ Large Yard Near Downtown!
9.8 out of 10, Exceptional, (40)
"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."
Historic Essex Home w/ Large Yard Near Downtown!
3Bed Hartford Condo Self Check in & Park
7.0 out of 10, Good, (2)
"Perfect for any travel situation. Neighborhood is very quiet during the day. Plenty of space. The property looks exactly as it does online."
The price is NZ$433
includes taxes & fees
2 Dec - 3 Dec
3Bed Hartford Condo Self Check in & Park
136 Raymond · Prime West Hartford Center Location: Historic Gem
10.0 out of 10, Exceptional, (17)
"This property and its location were perfect for our stay in Connecticut for family celebrations. Not only is West Hartford a great town to visit with all of its restaurants and shops, it’s close to the interstate and centrally located to many towns in north central CT that we were never more than 30 minutes from where we needed to be. "
136 Raymond · Prime West Hartford Center Location: Historic Gem
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.

Frequently asked questions

What is there to do in Portland near my cottage?
If you’d like to fill up your itinerary in Portland, make tracks to Brownstone Exploration & Discovery Park. It’s a winner among locals and tourists alike.