Photo by Rick Bucchino

Portland Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Portland

Interior
2-bedroom Oasis in Portland

2-bedroom Oasis in Portland

2.0 star property
Portland
The price is HK$1,225
HK$4,573 total
includes taxes & fees
18 Nov - 19 Nov
2-bedroom Oasis in Portland
Dining
#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat

Middletown
9.8 out of 10, Exceptional, (20)
"Great stay while our son moved into Wesleyan University. It was a nice alternative to staying at one of the local hotels. Clean and comfortable. We love the deck off the back with serene views of that lake. 5 minute drive to Wesleyan University. Will stay again for sure. "
United States
Allison C.
The price is HK$1,023
HK$2,420 total
includes taxes & fees
17 Nov - 18 Nov
#24 *Serenity* A Lakefront Cottage Retreat
Exterior
The Blue Back Bungalow

The Blue Back Bungalow

2.0 star property
West Hartford
9.4 out of 10, Exceptional, (16)
"Very clean, nicely appointed property. Cozy, nicely appointed and comfortable home to stay in for a family of four. Very nice little touches including cookies, chocolates, coffee/tea and fruit. I would stay here again."
United States
Bea F.
The price is HK$661
HK$2,465 total
includes taxes & fees
17 Nov - 18 Nov
The Blue Back Bungalow
Fridge, microwave, oven, stovetop
#23 *COMFORT & LUXURY* 3 BR/2 BA House

#23 *COMFORT & LUXURY* 3 BR/2 BA House

Southington
9.8 out of 10, Exceptional, (8)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is HK$1,073
HK$2,579 total
includes taxes & fees
17 Nov - 18 Nov
#23 *COMFORT & LUXURY* 3 BR/2 BA House
Exterior detail
Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!

East Haddam
9.4 out of 10, Exceptional, (34)
"The place was spotless and comfortable. Would highly recommend!"
United States
Jeanne Y.
The price is HK$1,298
HK$2,157 total
includes taxes & fees
1 Dec - 2 Dec
Walk To Goodspeed Opera House!
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Coventry Lake
9.8 out of 10, Exceptional, (34)
"The WiFi in the house was excellent. I was able to hold a Zoom meeting there. My husband and I chose the house because we love to swim. We did not expect that plants would be growing in the water, but we got used to walking and swimming through plants in shallow water to reach deeper water."
United States
Astrid L.
The price is HK$925
HK$2,175 total
includes taxes & fees
18 Nov - 19 Nov
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Coventry Lake
8.8 out of 10, Excellent, (48)
"Perfect for everything we needed. Cute and cozy, and 12 miles from our son’s home. Our granddaughter stayed over one of the nights and loved having her own space (she is 4). We Will definitely stay again. "
United States
Julie D.
The price is HK$925
HK$2,175 total
includes taxes & fees
17 Nov - 18 Nov
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Beach nearby
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Salem
10.0 out of 10, Exceptional, (4)
"Place is nice would stay again "
United States
nic
The price is HK$711
HK$2,779 total
includes taxes & fees
1 Dec - 2 Dec
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Exterior
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

Killingworth
10.0 out of 10, Exceptional, (51)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is HK$2,798
HK$5,379 total
includes taxes & fees
17 Nov - 18 Nov
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Fridge, microwave, oven, stovetop
Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location

Manchester Center
10.0 out of 10, Exceptional, (5)
"This house was perfect for the 4 of us. We all had our own bedroom and shared the bath. It’s very clean and close to everywhere we were going! The home is modern and the beds were comfy! I would stay there again. Great home! "
United States
Lorie D.
The price is HK$1,003
HK$2,280 total
includes taxes & fees
17 Nov - 18 Nov
Modern & Cozy Cape | 4 Bedroom House | Central Location
Interior
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, (26)
"The property was excellent. Quiet, comfortable and roomy. The bed was really comfortable and we have already booked to come back in July. The personal touches were wonderful. We loved the place, perfect been for 1 or 2 people."
United States
Victoria S.
The price is HK$972
HK$1,990 total
includes taxes & fees
23 Nov - 24 Nov
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
1 bedroom, iron/ironing board, WiFi, bed sheets
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, (13)
"The fact that it was listed with a hot tub and there wasn't one was very disappointing! Clean and cute. Location was convenient. Could use a better bed and pillows. It was a good place to stay,"
United States
Robert K.
The price is HK$715
HK$2,012 total
includes taxes & fees
17 Nov - 18 Nov
Once the old Schools house now a newly furnished Apartment
Outdoor dining
Soothing 2-bedroom lower-level apartment in Berlin

Soothing 2-bedroom lower-level apartment in Berlin

Berlin
10.0 out of 10, Exceptional, (1)
"This apartment was very clean and well-stocked. It was comfortable and cozy. It is in a great location in the center of Connecticut, a very nice, quiet neighborhood. We went on the hiking path just minutes from the front door. We went to Massachusetts, NYC, and Rhode Island, all were a hour and half or less away. In the backyard, we ate in the covered patio and sat around the firepit. There were top-notch grocery stores or dining options within five miles. Our host was responsive and caring. "
United States
Theresa G.
The price is HK$700
HK$2,163 total
includes taxes & fees
17 Nov - 18 Nov
Soothing 2-bedroom lower-level apartment in Berlin
Interior
Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

2.0 star property
Bloomfield
9.4 out of 10, Exceptional, (3)
"There were 7 of us staying for a Wedding near by. The home was bright, clean and very roomy. I would 100% stay here again. Host was on top of everything!! "
United States
Joslynn T.
The price is HK$1,710
HK$4,668 total
includes taxes & fees
25 Nov - 26 Nov
Modern Family Retreat | Near Downtown Hartford | Sleeps 10
Fridge, microwave, oven, coffee/tea maker
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
7.6 out of 10, Good, (7)
" Not bad for the price "
United States
Audrey L.
The price is HK$1,071
HK$2,891 total
includes taxes & fees
17 Nov - 18 Nov
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
Microwave, electric kettle, cookware/dishes/utensils, paper towels
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Downtown Hartford
9.6 out of 10, Exceptional, (5)
"The place is well located in the city and clean. “Parking available” does not mean free parking provided by the owner. There is metered street parking and pay parking garages."
United States
Nicholas
The price is HK$777
HK$1,496 total
includes taxes & fees
17 Nov - 18 Nov
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

All New 1BR with tons of Charm

Wallingford Center
9.8 out of 10, Exceptional, (6)
"This is a very nice updated one-bedroom apartment in a central location. Restaurants are within walking distance. The building has an elevator. The kitchen has everything you need. I enjoyed my stay. Just one caveat: the train tracks run just behind the building. The trains aren’t constant, but they do blow their horn at the intersection. I brought earplugs, and the noise didn’t keep me from sleeping "
United States
Karen D.
The price is HK$715
HK$2,012 total
includes taxes & fees
17 Nov - 18 Nov
All New 1BR with tons of Charm
Dining
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Coventry Lake
9.6 out of 10, Exceptional, (38)
"The property is great and has everything you need!"
United States
Adam L.
The price is HK$1,353
HK$2,721 total
includes taxes & fees
2 Dec - 3 Dec
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
The price is HK$909
HK$2,457 total
includes taxes & fees
17 Nov - 18 Nov
Private Apartment in Berlin
Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2.0 star property
East Haddam
9.6 out of 10, Exceptional, (80)
"Very nice cabins "
United States
Jairo
The price is HK$1,003
HK$1,511 total
includes taxes & fees
17 Nov - 18 Nov
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"The room was spotless and services were wonderful "
Bernard 1-night trip
Posted 2 days ago
Hampton Inn & Suites Hartford/East Hartford

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:

  • View our selection of featured holiday rentals in Portland
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Portland while they last

Look no further and take a look at our great range of rental properties in Portland!

Frequently asked questions

Are there holiday rentals in Portland?

Yes, there are holiday 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 are some of the best holiday rentals that Portland has to offer?

Private Apartment in Berlin: This holiday home rental outside of Portland is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 holiday rental in Portland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Portland. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for families.