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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Portland vacation rentals

Dining

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 AED 337
AED 901 total
includes taxes & fees
18 Aug - 19 Aug
2BR Apartment Near Wesleyan 102
Property grounds

2. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (24 reviews)
"It was great "
United States
Rodrigo C.
The price is AED 625
AED 1,332 total
includes taxes & fees
18 Aug - 19 Aug
#24 *Serenity* A Lakefront Cottage Retreat
Coffee/tea maker, fridge, microwave, oven

3. 2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (3 reviews)
"The living quarters was clean, no bugs, essentials provided (except laundry detergent and hair dryer), quiet residence, muddy parking lot, safe neighborhood, great communication and ease of parking and entry. "
United States
Joanne L.
The price is AED 415
AED 1,102 total
includes taxes & fees
19 Aug - 20 Aug
2BR Apartment Near Wesleyan 301
Dining

4. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (1 review)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is AED 500
AED 1,210 total
includes taxes & fees
19 Aug - 20 Aug
3 BR Apartment Near Wesleyan 201
View from property

5. 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, (179 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 AED 496
AED 909 total
includes taxes & fees
20 Aug - 21 Aug
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Coffee/tea maker, fridge, microwave, oven

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 AED 337
AED 1,008 total
includes taxes & fees
18 Aug - 19 Aug
Private Apt in Middletown-Wesleyan 101
Smart TV, fireplace, books, music library

7. 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, (35 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 AED 459
AED 948 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Coffee/tea maker, fridge, microwave, oven

8. “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 AED 840
AED 1,072 total
includes taxes & fees
31 Aug - 1 Sep
“3BR Home Near Wesleyan & Downtown Middletown
Dining

9. 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 AED 683
AED 1,596 total
includes taxes & fees
18 Aug - 19 Aug
3 BR Apartment Near Wesleyan 202
Property grounds

10. 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 AED 529
AED 1,156 total
includes taxes & fees
7 Sep - 8 Sep
Lakeview Carriage House with Spectacular Sunset Views
Interior

11. 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 AED 512
AED 1,140 total
includes taxes & fees
14 Sep - 15 Sep
Private Apartment in Berlin
Exterior

12. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AED 433
AED 1,086 total
includes taxes & fees
19 Aug - 20 Aug
All New 1BR with tons of Charm
Coffee/tea maker, fridge, microwave, oven

13. Fully Furnished 1BR Apartment

Fully Furnished 1BR Apartment
Wallingford
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay in town when visiting family! Kitchen was well stocked, location was convenient, & it had everything we needed!"
United States
Jennifer L.
The price is AED 433
AED 1,082 total
includes taxes & fees
6 Sep - 7 Sep
Fully Furnished 1BR Apartment
Interior

14. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is AED 2,644
AED 3,419 total
includes taxes & fees
17 Aug - 18 Aug
Conference Room Rental no sleeping arrangements
Dining

15. 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)
" Not bad for the price "
United States
Audrey L.
The price is AED 506
AED 1,366 total
includes taxes & fees
17 Aug - 18 Aug
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
TV

16. All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
The price is AED 433
AED 1,086 total
includes taxes & fees
20 Aug - 21 Aug
All New Private and Cozy in great location
TV

17. 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 apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is AED 433
AED 1,086 total
includes taxes & fees
10 Sep - 11 Sep
Newly Remodeled with deck. Close to town center
Interior

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 AED 253
AED 932 total
includes taxes & fees
19 Aug - 20 Aug
The Sun Filled Cozy Creamery
1 bedroom, iron/ironing board, WiFi, bed sheets

19. 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 AED 433
AED 1,082 total
includes taxes & fees
30 Aug - 31 Aug
Once the old Schools house now a newly furnished Apartment
Smart TV, offices

20. Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
10.0 out of 10, Exceptional, (1 review)
"Perfect place for a quick stay"
United States
phillip s.
The price is AED 317
AED 776 total
includes taxes & fees
17 Aug - 18 Aug
Crested One Place - with Free Parking, Heat & AC
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
"It's Amazing Good staff!!!!!!!?"
Zolunda 3-night trip
Posted less than an hour ago
Best Western Hartford Hotel & Suites

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.