Portland Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Portland vacation rentals

Beach nearby

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.2 out of 10, Wonderful, (40 reviews)
"Pet and family, friendly"
United States
Mary-Kate G
The price is ￥17,020
￥42,458 total
includes taxes & fees
Apr 13 - Apr 14
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
View from property

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, (132 reviews)
"Our favorite place to visit ♥️"
United States
Teresa
The price is ￥17,426
￥27,351 total
includes taxes & fees
Apr 16 - Apr 17
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Smart TV, computer monitors

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 ￥13,707
￥32,927 total
includes taxes & fees
Apr 12 - Apr 13
Central Chic Pad - with Free Parking, Heat & AC
Smart TV

Crested One Place - with Free Parking, Heat & AC

Crested One Place - with Free Parking, Heat & AC
Manchester
The price is ￥13,707
￥32,927 total
includes taxes & fees
Apr 13 - Apr 14
Crested One Place - with Free Parking, Heat & AC
Interior

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Manchester Center
10.0 out of 10, Exceptional, (8 reviews)
"excellent location, cozy apartment"
United States
Monica H.
The price is ￥19,865
￥32,420 total
includes taxes & fees
Apr 12 - Apr 13
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester
Interior

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

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Salem
9.8 out of 10, Exceptional, (9 reviews)
"Place is nice would stay again "
United States
nic
The price is ￥22,224
￥66,132 total
includes taxes & fees
May 4 - May 5
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Smart TV

Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut
South Windsor
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at this clean, cozy and well-decorated guest suite! Our host was very welcoming, and quickly responded to inquiries and messages. We would definitely plan to return here if we’re back in the area!"
United States
Jan E.
The price is ￥13,731
￥18,969 total
includes taxes & fees
Apr 19 - Apr 20
Entire guest suite in South Windsor, Connecticut
2 bedrooms, WiFi, bed sheets

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (6 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is ￥14,589
￥38,232 total
includes taxes & fees
Apr 9 - Apr 10
Private Apartment in Berlin
Smart TV

15mins to Hartford, Home in Manchester w/ King Bed

15mins to Hartford, Home in Manchester w/ King Bed
Manchester
9.2 out of 10, Wonderful, (7 reviews)
"Check in easy, great communications - very quick & answered any questions. Great location for what we needed, layout of house was perfect for us, Roku let us stream all the shows we wanted to watch. Ate out so didn’t use kitchen a lot, beds were comfortable. When we come back to visit our daughter will use again. "
United States
mike p.
The price is ￥28,102
￥56,268 total
includes taxes & fees
Apr 9 - Apr 10
15mins to Hartford, Home in Manchester w/ King Bed
Fridge, microwave, oven, stovetop

2BR Apartment Near Wesleyan 301

2BR Apartment Near Wesleyan 301
Washington Street Historic District
10.0 out of 10, Exceptional, (2 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 ￥19,706
￥49,043 total
includes taxes & fees
Apr 13 - Apr 14
2BR Apartment Near Wesleyan 301
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (35 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is ￥18,117
￥33,310 total
includes taxes & fees
Apr 16 - Apr 17
Walk To Goodspeed Opera House!
Property grounds

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"The house was cozy and comfortable. The location was great while dropping our son off at Wesleyan University for his sophomore year. The lake was a peaceful place to relax and read."
United States
julia h.
The price is ￥30,036
￥60,763 total
includes taxes & fees
Apr 11 - Apr 12
#24 *Serenity* A Lakefront Cottage Retreat
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, (37 reviews)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is ￥16,401
￥40,792 total
includes taxes & fees
Apr 9 - Apr 10
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Living area

Fully Furnished Private Loft Style Charm Trumbull Elevator

Fully Furnished Private Loft Style Charm Trumbull Elevator
Downtown Hartford
The price is ￥15,097
￥35,320 total
includes taxes & fees
Apr 14 - Apr 15
Fully Furnished Private Loft Style Charm Trumbull Elevator
Fridge, microwave, stovetop, coffee/tea maker

Charming Luxury 1BR Near Downtown. Dog Friendly!

Charming Luxury 1BR Near Downtown. Dog Friendly!
Manchester
9.4 out of 10, Exceptional, (12 reviews)
"Amazing stay. Easy check-in/access and Karl was quick to answer any questions I had. The place was immaculate, clean and modern with all the amenities you’ll need. Very convenient and walkable to coffee shops, bars & restaurants. We’ll be back."
United States
Todd L.
The price is ￥12,586
￥47,569 total
includes taxes & fees
Apr 15 - Apr 16
Charming Luxury 1BR Near Downtown. Dog Friendly!
Interior

Stylish Townhome | Perfect for Family Gatherings & Events

Stylish Townhome | Perfect for Family Gatherings & Events
Bloomfield
10.0 out of 10, Exceptional, (5 reviews)
"The house was newer and the living room and kitchen had open layout that enabled to spend quality time with family."
United States
Muhammad G.
The price is ￥69,400
￥139,803 total
includes taxes & fees
Apr 11 - Apr 12
Stylish Townhome | Perfect for Family Gatherings & Events
Smart TV

Charming 3-Bedroom Home with Modern Comforts in West Hartford

Charming 3-Bedroom Home with Modern Comforts in West Hartford
West Hartford
8.2 out of 10, Very Good, (10 reviews)
"Great house in a safe neighborhood with a fenced in yard. Amenities provided. "
United States
Ben H.
The price is ￥22,482
￥49,166 total
includes taxes & fees
Apr 9 - Apr 10
Charming 3-Bedroom Home with Modern Comforts in West Hartford
Property grounds

Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is ￥19,070
￥25,109 total
includes taxes & fees
Apr 9 - Apr 10
Humble Abode #2
Interior

Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location
Manchester Center
10.0 out of 10, Exceptional, (8 reviews)
"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 ￥20,501
￥45,825 total
includes taxes & fees
Apr 22 - Apr 23
Modern & Cozy Cape | 4 Bedroom House | Central Location
Smart TV, fireplace, books, music library

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, (29 reviews)
"Fantastic experience from beginning to end! Loved every minute of my stay! "
United States
Jody U.
The price is ￥19,865
￥40,207 total
includes taxes & fees
Apr 15 - Apr 16
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Clean lobby and great hotel staff. Hall way carpets could use a clean "
Sammy 1-night trip
Posted 3 hours ago
Holiday Inn Express Southington by IHG

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 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?

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford: This vacation home rental outside of Portland has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.