A river with a large bridge and a small boat on the shore.

Search Portland Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Portland cottages

Exterior

Go Jump in the Lake!

Go Jump in the Lake!
Lebanon
10.0 out of 10, Exceptional, (157 reviews)
"The stay was clean and neat, the host responded to messages quickly, very enjoyable to stay for the weekend!"
United States
Manny D.
$343 nightly
The price is $388
Jul 26 - Jul 27
Total with taxes and fees
Go Jump in the Lake!
Exterior

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

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Lake Pocotopaug
10.0 out of 10, Exceptional, (18 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
$295 nightly
The price is $334
Aug 3 - Aug 4
Total with taxes and fees
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Interior

Privet Farm cottage with AC and Deck in charming Salem Connecticut

Privet Farm cottage with AC and Deck in charming Salem Connecticut
Salem
$287 nightly
The price is $324
Jul 19 - Jul 20
Total with taxes and fees
Privet Farm cottage with AC and Deck in charming Salem Connecticut
House (3 Bedrooms) | Interior

Lakefront Home, Close to Mt Southington!

Lakefront Home, Close to Mt Southington!
3.0 star property
Wolcott
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house with great views of the lake. "
United States
Darrell
$425 nightly
The price is $489
Aug 3 - Aug 4
Total with taxes and fees
Lakefront Home, Close to Mt Southington!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Portland Hotel Reviews

Ramada by Wyndham Hartford North / Bradley Airport

Ramada by Wyndham Hartford North / Bradley Airport

8/10 Good
"Helpful"
Andre 1-night trip
Posted 15 hours ago
Ramada by Wyndham Hartford North / Bradley Airport

Find out more about Portland

Portland Cottages information

Number of reviews
178
Accommodation
49 Cottages
Lowest Price
$324
Highest Price
$489

Frequently asked questions

Why book your cottage in Portland with Expedia?
Reserving a cottage in Portland is as easy as entering your travel dates and choosing an ideal place for a vacation in the outdoors. From ritzy retreats to inexpensive properties and cottages that feature perks like a hot tub, Expedia has something for all traveler tastes. As for irresistible deals? We've got you covered!
How can I find cheap cottages in Portland?
Expedia can help you track down cheap cottages in Portland. To discover a superb stay in just a few clicks, simply use the filter tool to refine your search by star rating, amenities and budget.
What is there to do in Portland near my cottage?
If you're ready to explore the best of Portland, don't miss Brownstone Exploration & Discovery Park. It's popular among locals and visitors alike.

Explore a world of travel with Expedia