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

Portland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Portland vacation rentals

A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

1. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (5 reviews)
The price is ￥21,673
￥47,983 total
includes taxes & fees
Aug 31 - Sep 1
2BR Apartment Near Wesleyan 102
A cabin with a large window, surrounded by trees.

2. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (183 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
The price is ￥20,171
￥37,849 total
includes taxes & fees
Sep 2 - Sep 3
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

3. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (36 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is ￥19,909
￥41,092 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A dining room with a rectangular table and four chairs, a window with blinds, a recessed ceiling light, and a wall-mounted air conditioning unit.

4. 3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202
Washington Street Historic District
8.0 out of 10, Very Good, (1 review)
"The apartment is the first floor of a two story duplex. It was very clean and larger than we were expecting. We had just about everything we needed for our stay. We really appreciate being able to bring our pets with us. I enjoyed walking around the neighborhood with my dog."
United States
Douglas M.
The price is ￥31,553
￥71,425 total
includes taxes & fees
Aug 31 - Sep 1
3 BR Apartment Near Wesleyan 202
A modern kitchen with white cabinets, a stainless steel refrigerator, a dining area with two chairs, and a coffee machine.

5. “3BR Home Near Wesleyan & Downtown Middletown

“3BR Home Near Wesleyan & Downtown Middletown
Washington Street Historic District
7.8 out of 10, Good, (6 reviews)
"Nice place"
United States
Jousette C.
The price is ￥35,856
￥46,175 total
includes taxes & fees
Aug 31 - Sep 1
“3BR Home Near Wesleyan & Downtown Middletown
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

6. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.0 out of 10, Good, (4 reviews)
"Very clean. No frills."
United States
Kristoph
The price is ￥21,514
￥52,310 total
includes taxes & fees
Aug 31 - Sep 1
Private Apt in Middletown-Wesleyan 101
A lakeside property with a gazebo, dock, kayaks, and a flag.

7. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is ￥24,701
￥52,629 total
includes taxes & fees
Sep 7 - Sep 8
Lakeview Carriage House with Spectacular Sunset Views
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

8. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is ￥28,047
￥61,098 total
includes taxes & fees
Sep 22 - Sep 23
3 BR Apartment Near Wesleyan 201

9. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
The price is ￥21,354
￥48,302 total
includes taxes & fees
Sep 16 - Sep 17
Private Apartment in Berlin
A modern living room with a sofa, a dining table, and a massage chair.

10. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.4 out of 10, Exceptional, (6 reviews)
"Great place! "
United States
Gail R.
The price is ￥50,955
￥97,301 total
includes taxes & fees
Sep 23 - Sep 24
#29 - Modern 5 Bedroom/2 Bath

11. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Very nice! Clean and had everything you would need for a few nights away from home. I book again. "
United States
ALRUNDUS L.
The price is ￥18,794
￥47,096 total
includes taxes & fees
Aug 31 - Sep 1
All New 1BR with tons of Charm
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

12. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
United States
Linda v.
The price is ￥18,794
￥46,937 total
includes taxes & fees
Sep 25 - Sep 26
Newly Remodeled 1-BR Close to Everything yet Very Private
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

13. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is ￥18,794
￥47,096 total
includes taxes & fees
Sep 10 - Sep 11
All New Studio apartment in center of town
A living room with a grey sofa, yellow cushions, a wooden coffee table, a TV on a stand, and a lamp on a side table.

14. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥18,804
￥47,122 total
includes taxes & fees
Sep 10 - Sep 11
Newly Remodeled with deck. Close to town center
A living room with a dining area, a TV, and a large window with a view of buildings.

15. Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is ￥13,737
￥33,795 total
includes taxes & fees
Aug 31 - Sep 1
Central Chic Pad - with Free Parking, Heat & AC
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

16. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is ￥18,804
￥47,122 total
includes taxes & fees
Aug 30 - Aug 31
Once the old Schools house now a newly furnished Apartment
A modern living room with a glass dining table, dark chairs, a sofa, and a ceiling fan.

17. Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment

Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
New Britain
6.8 out of 10, (8 reviews)
The price is ￥21,939
￥59,234 total
includes taxes & fees
Sep 4 - Sep 5
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
A hallway with a patterned wall, a wooden floor, a rug, a door with a wreath, and a bed visible through a glass door.

18. The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
9.0 out of 10, Wonderful, (26 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is ￥10,996
￥40,435 total
includes taxes & fees
Aug 30 - Aug 31
The Sun Filled Cozy Creamery
A modern office space with a sofa, two round tables, and a coffee table. There are chairs around the tables, a rug on the floor, and a door in the background.

19. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is ￥114,739
￥148,364 total
includes taxes & fees
Aug 29 - Aug 30
Conference Room Rental no sleeping arrangements
A two-story house with a front porch, a garage, and a well-maintained lawn.

20. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.8 out of 10, Exceptional, (17 reviews)
"Large, comfortable house in a tranquil part of town. "
United States
Daryl R.
The price is ￥81,132
￥140,963 total
includes taxes & fees
Sep 26 - Sep 27
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
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

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

10/10 Excellent
"Comfortable"
Michael 3-night trip
Posted 1 hour ago
HYATT house Hartford North/Windsor

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Portland?

Yes, you can find vacation rentals in Portland close to Brownstone Exploration & Discovery Park, or you can select a more secluded option if you're looking for a relaxing stay. Portland is known for its riverfront and wineries. Make sure you have time to check out the theme park and restaurants during your trip.

What's the top vacation rental in Portland?

NEW Coastal Cottage 2 Miles to Beach + Lake Access: This vacation home rental outside of Portland is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What’s there to see and do in Portland?

Family-friendly attractions include Brownstone Exploration & Discovery Park, whereas Connecticut River is a spot to enjoy the outdoors. Arrigoni Winery and Chris Cote's Toptracer Golf Range and Performance Center are other places to visit while you're in town.

What’s a vacation rental in Portland like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Portland. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.