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

Holiday Rentals in Portland

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Portland holiday rentals

A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

1. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is €354
includes taxes & fees
20 Sept - 21 Sept
#24 *Serenity* A Lakefront Cottage Retreat
A modern kitchen with dark cabinetry, a marble countertop, and a dining area with a table and chairs.

2. 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 €363
includes taxes & fees
15 Sept - 16 Sept
3 BR Apartment Near Wesleyan 201
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

3. 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 €280
includes taxes & fees
24 Sept - 25 Sept
2BR Apartment Near Wesleyan 102
A cabin with a large window, surrounded by trees.

4. 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, (184 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is €213
includes taxes & fees
30 Sept - 1 Oct
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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.
“3BR Home Near Wesleyan & Downtown Middletown
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.

6. Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements
Main Street Historic District
The price is €799
includes taxes & fees
2 Sept - 3 Sept
Conference Room Rental no sleeping arrangements
A two-story house with a front porch, a garage, and a well-maintained lawn.

7. 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
9.6 out of 10, Exceptional, (18 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
The price is €754
includes taxes & fees
14 Sept - 15 Sept
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A modern kitchen with a central island, bar stools, and pendant lighting.

8. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (30 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
The price is €896
includes taxes & fees
2 Sept - 3 Sept
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & 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.

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 €326
includes taxes & fees
2 Sept - 3 Sept
3 BR Apartment Near Wesleyan 202
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.

10. 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 €234
includes taxes & fees
15 Sept - 16 Sept
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A lakeside property with a gazebo, dock, kayaks, and a flag.

11. 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 €273
includes taxes & fees
7 Sept - 8 Sept
Lakeview Carriage House with Spectacular Sunset Views
A compact kitchen with white cabinets, a built-in oven, and a dining table with chairs.

12. 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 €285
includes taxes & fees
2 Sept - 3 Sept
Private Apt in Middletown-Wesleyan 101
A bedroom with a bed, a round table, a grey sofa, a window with a view of buildings, and a wooden wardrobe.

13. Trumbull Apartments

Trumbull Apartments
3.0 star property
Downtown Hartford
2.0 out of 10, (1 review)
"Terrible, worst stay ever . It was such a hassle to get in no clear instructions… never again"
United States
Nicolas
The price is €292
includes taxes & fees
2 Sept - 3 Sept
Trumbull Apartments

14. 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 €260
includes taxes & fees
2 Sept - 3 Sept
All New 1BR with tons of Charm

15. 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 €268
includes taxes & fees
21 Sept - 22 Sept
Private Apartment in Berlin
A spacious living room with hardwood flooring, a grey sofa, a coffee table, and a chandelier.

16. West Hartford Center: Charming New England Apt

West Hartford Center: Charming New England Apt
West Hartford
10.0 out of 10, Exceptional, (9 reviews)
"Immaculate, nice decor, very comfortable beds, every detail is well thought out. "
United States
Cathryna B.
The price is €433
includes taxes & fees
3 Sept - 4 Sept
West Hartford Center: Charming New England Apt
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)
" Not bad for the price "
United States
Audrey L.
The price is €315
includes taxes & fees
14 Sept - 15 Sept
Two Families, up and Down Stairs, the 2nd Floor is the Vrbos Apartment
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

18. 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)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is €260
includes taxes & fees
20 Sept - 21 Sept
Newly Remodeled 1-BR Close to Everything yet Very Private
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

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 €260
includes taxes & fees
2 Sept - 3 Sept
Once the old Schools house now a newly furnished Apartment
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

20. 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 €260
includes taxes & fees
2 Sept - 3 Sept
All New Studio apartment in center of town
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
"Very surprised about everything compared hotels close by that have stayed at. We'll be back again forsure. Thank for the staffs dedication"
Dave 2-night trip
Posted 4 hours ago
HYATT house Hartford North/Windsor

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as €140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This holiday home rental outside of Portland has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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.