Vacation rentals in Portland
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Top-rated vacation rentals in Portland
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Portland vacation rentals
Other great vacation rentals in Portland
Guest favorite
Guest suite in Portland
4.92 out of 5 average rating, 12 reviewsCozy waterview in-law apartment
Oct 16 – 23
$111 per night
Guest favorite
Guesthouse in Portland
5.0 out of 5 average rating, 70 reviewsGuesthouse Farm Stay
Nov 20 – 27
$131 per night
Guest favorite
Farm stay in Glastonbury
5.0 out of 5 average rating, 56 reviewsHistoric Farmhouse by the River (Duplex)
Sep 9 – 16
$111 per night
Guest favorite
Home in Haddam
5.0 out of 5 average rating, 78 reviewsCozy Comforts!
Jan 20 – 27
$89 per night
Guest favorite
Home in Middletown
5.0 out of 5 average rating, 12 reviewsHome with Fiber Optic Internet
Oct 16 – 23
$134 per night
Guest favorite
Home in East Hampton
4.95 out of 5 average rating, 21 reviewsWaterfront Lake House
Mar 19 – 26
$446 per night
Guest favorite
Vacation home in East Hampton
5.0 out of 5 average rating, 25 reviewsFamily Friendly Lake House Lake Pocotopaug Sunsets
May 8 – 15
$388 per night
Guest favorite
Home in East Hampton
4.98 out of 5 average rating, 51 reviewsLake Fun: PingPong, Pool Table, Slide, EV Charger
Mar 10 – 17
$271 per night
Quick stats about vacation rentals in Portland
Total rentals
20 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
1.2K reviews
Nightly prices starting at
$50 before taxes and fees
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