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Portland Vacation Rentals

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Vacation Rentals in Portland

Fun Downtown Location
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, 49 reviews
"Nice space with 3 roomy bedrooms. Plenty of storage for clothes. Bathroom is small but not untypical of this era home. Steps to second floor are steep, so consider this. Kitchen has what you need for a short stay."
Fun Downtown Location
Charming 2 Bedroom Guest Apartment in Essex, CT
Property grounds
Charming 2 Bedroom Guest Apartment in Essex, CT
10.0 out of 10, Exceptional, 20 reviews
"The host had so many special touches to make this place a wonderful spot to stay. She had little snacks in the kitchen, with coffee and tea in the cupboard. There was half-and-half and the refrigerator, which we really appreciated. The towels in the bathroom were folded like you were in a special hotel. There was also lovely soap, shampoo and conditioner. Due to the cold temperature in the teens, she actually purchased some space heaters to make sure we were warm. Although there was a second...
Charming 2 Bedroom Guest Apartment in Essex, CT
Go Jump in the Lake!
Go Jump in the Lake!
10.0 out of 10, Exceptional, 127 reviews
"House was very clean, well equipped and had everything we needed to enjoy a relaxing getaway as a family. We enjoyed the firepit, covered porch and lakeside fun."
The price is ￥22,456
per night
Jun 12 - Jun 13
Go Jump in the Lake!
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Lakefront Cottage w/ Covered Porch & Dock!
Interior
Lakefront Cottage w/ Covered Porch & Dock!
3.0 star property
Lakefront Cottage w/ Covered Porch & Dock!
Mountaintop Horse Farm with Heated Pool
Outdoor pool, a heated pool
Mountaintop Horse Farm with Heated Pool
10.0 out of 10, Exceptional, 15 reviews
"Thank you for a lovely home to stay in during our family funeral weekend!"
Mountaintop Horse Farm with Heated Pool
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
Fridge, microwave, oven, stovetop
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
9.6 out of 10, Exceptional, 26 reviews
"Joe was very attentive and left the house very clean for us. Definitely worth the money"
The price is ￥30,402
per night
Jun 9 - Jun 10
Lake | PetsOK | Wi-Fi | W&D | Fire Pit | Kayaks
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
9.0 out of 10, Wonderful, 2 reviews
"This was easily accessible to many places and the check-in process and communications with the owner were exceptional. Great place to stay."
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Exterior
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, 106 reviews
"Very nice stay. Only disappointment was the lack of a hot tub. Otherwise a perfect venue for our group."
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.8 out of 10, Exceptional, 8 reviews
"This is an immaculate guest suite with incredible views in a gorgeous setting. The owners were extremely responsive and communicative, enhancing our stay. The bed is very comfortable and the appliances and just about everything looks brand new. The grounds, pool area and views are amazing. If you’re looking for a comfortable and peaceful stay in a relaxing setting, this is the place! Your hosts will make sure you are well taken care of."
The price is ￥35,465
per night
Jul 1 - Jul 2
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Fridge, microwave, oven, stovetop
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, 1 review
"Beautiful new home and property! Would one back for sure!"
The price is ￥92,922
per night
Jun 9 - Jun 10
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Massive 5 Bedrooms: 3King 2Queen
Fridge, microwave, oven, stovetop
Massive 5 Bedrooms: 3King 2Queen
The price is ￥54,194
per night
Jun 11 - Jun 12
Massive 5 Bedrooms: 3King 2Queen
Amazing Lakefront Property
Smart TV, fireplace, offices
Amazing Lakefront Property
10.0 out of 10, Exceptional, 15 reviews
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Aerial view
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, 8 reviews
"Adorable cottage with full kitchen, luxurious bathroom and comfiest beds!! Cutest cul de sac with friendly neighbors"
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
lakefront estate
Pool
lakefront estate
3.8 out of 10, 8 reviews
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
comfortable home away from home
Fridge, microwave, oven, stovetop
comfortable home away from home
9.2 out of 10, Wonderful, 5 reviews
"This little house is tucked behind some bigger neighbors. It was comfortable and quiet! We had a ball watching the antics of a family of squirrels. It fit our needs perfectly!"
comfortable home away from home
Lakefront | King | W&D | Fire Pit | Kayaks | SUPs
Fridge, microwave, oven, stovetop
Lakefront | King | W&D | Fire Pit | Kayaks | SUPs
9.8 out of 10, Exceptional, 14 reviews
"It a cute cottage style house that is steps away from a beach on the lake. Very close to the neighbors. If you play the record player you will cause a noise alarm to go off which I was not aware of prio to staying there."
The price is ￥39,647
per night
Jun 18 - Jun 19
Lakefront | King | W&D | Fire Pit | Kayaks | SUPs
The getaway! Located in the downtown area.
Fridge, microwave, oven, stovetop
The getaway! Located in the downtown area.
10.0 out of 10, Exceptional, 7 reviews
"This home was very nicely updated with new pillows, comfy bed and well stocked kitchen. Perfect location near the hospital"
The price is ￥24,315
per night
Jul 2 - Jul 3
The getaway! Located in the downtown area.
Luxurious midcentury modern glass house in the woods, chefs kitchen & great art
Property grounds
Luxurious midcentury modern glass house in the woods, chefs kitchen & great art
10.0 out of 10, Exceptional, 1 review
"This home was the perfect place for us to stay. It felt cozy and spacious at the same time. We had two couples, two kiddos and one single and had plenty of space to do our own things as well as cozy areas to just hang out and enjoy our time all together."
Luxurious midcentury modern glass house in the woods, chefs kitchen & great art
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Fridge, microwave, oven, stovetop
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
10.0 out of 10, Exceptional, 7 reviews
"Quiet,peaceful,clean, friendly,cozy!!!!"
The price is ￥19,359
per night
Jun 17 - Jun 18
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Historic 4 Bedroom Luxury Cabin with Private Waterfall & Lake Access
Property grounds
Historic 4 Bedroom Luxury Cabin with Private Waterfall & Lake Access
9.0 out of 10, Wonderful, 15 reviews
"Our family stayed at this property while enjoying family weekend at UConn. The home was a nice distance between campus and fun activities. The house was clean and well stocked with amenities. We missed having a hot tub as was the reason we chose this home, but the views in the backyard were beautiful. We had a wonderful stay. Thank you!"
Historic 4 Bedroom Luxury Cabin with Private Waterfall & Lake Access
Don't see what you're looking for?
See all available properties in Portland
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.

Other types of properties in Portland you may be interested in

Solano Inn
Lake
Solano Inn
2.5 star property
7.6 out of 10, Good, 245 reviews
"The outside of the building is nothing like the inside. The room was great would stay there again for sure."
The price is ￥20,398
per night
Jun 23 - Jun 24
Solano Inn
Holiday Inn Express Southington, an IHG Hotel
Exterior
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very Good, 1,008 reviews
"It was clean "
The price is ￥22,139
per night
Jun 30 - Jul 1
Holiday Inn Express Southington, an IHG Hotel
Best Western Hartford Hotel & Suites
Lobby
Best Western Hartford Hotel & Suites
2.5 star property
8.0 out of 10, Very Good, 1,007 reviews
"Was quick & comfortable. Would have preferred water in the room "
The price is ￥13,691
per night
Jun 23 - Jun 24
Best Western Hartford Hotel & Suites
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.

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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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?

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!: This vacation 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. In the larger area, you’ll find Arrigoni Winery and Connecticut River State Wildlife Area.

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.

Recent reviews of Portland properties
Expedia verified reviews

DoubleTree by Hilton Hartford Downtown

DoubleTree by Hilton Hartford Downtown

5/5 Excellent
"Comfortable and clean. Front desk was friendly "
A verified traveler from Newburgh stayed at DoubleTree by Hilton Hartford Downtown
Posted 2 days ago
DoubleTree by Hilton Hartford Downtown