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Cottages in Portland

Upscale Waterbury Retreat w/ Indoor Hot Tub!
House (3 Bedrooms) | Interior

Upscale Waterbury Retreat w/ Indoor Hot Tub!

3.0 star property
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Elegant Middlefield Getaway w/ Game Room!
House (4 Bedrooms) | Interior

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Charming Windsor Home w/ Private Backyard!
House (3 Bedrooms) | Interior

Charming Windsor Home w/ Private Backyard!

3.0 star property
8.0 out of 10, Very Good, (1)
"The property was exactly as advertised and what we needed for a two night stay for a graduation. It was economical and accommodated 5 people comfortably. The interior is a bit dated, but clean. We did not spend much time at the property, so it worked well for us. The beds were a bit hard, but functional for two nights."
Charming Windsor Home w/ Private Backyard!
Modern Terryville Cottage w/ Deck & Lake View!
Interior

Modern Terryville Cottage w/ Deck & Lake View!

3.0 star property
10.0 out of 10, Exceptional, (1)
Modern Terryville Cottage w/ Deck & Lake View!
Pet-friendly Lebanon House w/ Lake Access!
House (3 Bedrooms) | Interior

Pet-friendly Lebanon House w/ Lake Access!

3.0 star property
Pet-friendly Lebanon House w/ Lake Access!
Lakefront Connecticut Retreat Near Uconn
Cottage (2 Bedrooms) | Interior

Lakefront Connecticut Retreat Near Uconn

3.0 star property
Lakefront Connecticut Retreat Near Uconn
Charming Farmhouse w/ Pool & Fishing Pond!
House (5 Bedrooms) | Interior

Charming Farmhouse w/ Pool & Fishing Pond!

3.0 star property
Charming Farmhouse w/ Pool & Fishing Pond!
Lakefront Home, Close to Mt Southington!
House (3 Bedrooms) | Interior

Lakefront Home, Close to Mt Southington!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful house with great views of the lake. "
Lakefront Home, Close to Mt Southington!
Historic Essex Home w/ Large Yard Near Downtown!
House (2 Bedrooms) | Interior

Historic Essex Home w/ Large Yard Near Downtown!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing Host. Fantastic trip "
Historic Essex Home w/ Large Yard Near Downtown!
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
Dining

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

3.0 star property
Cozy Lakefront Cottage w/ Fire Pit, Grill & Views!
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
Lakefront Cottage w/ Covered Porch & Dock!
Cottage (3 Bedrooms) | Interior

Lakefront Cottage w/ Covered Porch & Dock!

3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
BBQ Ready: Quiet Connecticut Retreat w/ Fire Pit
House (4 Bedrooms) | Interior

BBQ Ready: Quiet Connecticut Retreat w/ Fire Pit

3.0 star property
BBQ Ready: Quiet Connecticut Retreat w/ Fire Pit
Luxe Lake House in Connecticut: Private Dock
Microwave, oven, stovetop, dishwasher

Luxe Lake House in Connecticut: Private Dock

3.0 star property
Luxe Lake House in Connecticut: Private Dock
Lakefront Home: 2 Mi to Air Line State Park Trail!
Terrace/patio

Lakefront Home: 2 Mi to Air Line State Park Trail!

3.0 star property
Lakefront Home: 2 Mi to Air Line State Park Trail!
Group Getaway w/ Outdoor Oasis in Southington!
House (4 Bedrooms) | Interior

Group Getaway w/ Outdoor Oasis in Southington!

3.0 star property
Group Getaway w/ Outdoor Oasis in Southington!
Spacious East Haddam Retreat w/ Private Pool!
Interior

Spacious East Haddam Retreat w/ Private Pool!

3.0 star property
Spacious East Haddam Retreat w/ Private Pool!
10 Mi to Hartford: Family Home w/ Yard
House (3 Bedrooms) | Interior

10 Mi to Hartford: Family Home w/ Yard

3.0 star property
10 Mi to Hartford: Family Home w/ Yard
Family Getaway in Bristol Near Trails & Parks!
Interior

Family Getaway in Bristol Near Trails & Parks!

3.0 star property
Family Getaway in Bristol Near Trails & Parks!
Cottage-chic Retreat < 1 Mi to Connecticut River!
House (3 Bedrooms) | Interior

Cottage-chic Retreat < 1 Mi to Connecticut River!

3.0 star property
Cottage-chic Retreat < 1 Mi to Connecticut River!
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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Top Portland Hotel Reviews

Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

10/10 Excellent
"everything good morning "
Ernesto 3-night trip
Posted 11 hours ago
Best Western Hartford Hotel & Suites

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.