Holiday rentals in Portland

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Top-rated holiday rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Flat in Portland
Spacious and Comfortable Private Apartment
Third floor (i.e. a few stairs) spacious apartment with a private entrance. Walking distance to Thompson’s Point, Maine Med and many other trails and attractions. The Old Port is a 5 minute drive (1.5 mi.). There is plenty of free street parking available. Space heaters warm the space in the winter, and a/c is provided in the summer. The house is shared by first floor tenants while our family occupies the second floor. Again, several stairs to navigate, but quite comfortable once you settle in!
4–11 Nov
$88 SGD per night
4.82 out of 5 average rating, 347 reviews
Guest favourite
Guest house in Portland
Beautiful large studio on the ocean.
Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.
28 Apr – 5 May
$179 SGD per night
4.95 out of 5 average rating, 277 reviews
Guest favourite
Flat in Portland
RETRO BnB in the Heart of East End Portland
Retro BnB in The Heart of Portland's East End offers a combination of 70's mod charm with a vibrant comfortable style. Sunny, first floor back apartment with private entrance, one hybrid coil/thermarest queen bed overlooking yard with lovely perennial garden, bathroom with central, well appointed kitchen/dining room. This space is perfect for one couples looking for a cozy home base hideaway. A short walk to gourmet restaurants, cafes, East End beach and all Portland peninsula has to offer!
3–10 May
$187 SGD per night
4.97 out of 5 average rating, 372 reviews

Popular amenities for Portland holiday rentals

Stay near Portland's top sights

Peaks Island176 locals recommend
The Maine Mall86 locals recommend
Portland International Jetport50 locals recommend
Fort Williams Park229 locals recommend
Portland Observatory132 locals recommend
Allagash Brewing Company156 locals recommend

Other great holiday rentals in Portland

Guest favourite
Guest house in Cape Elizabeth
Newly built private guest suite off Shore Road
6–13 May
$176 SGD per night
4.98 out of 5 average rating, 138 reviews
Guest favourite
Flat in Portland
Crow's Nest
8–15 May
$390 SGD per night
4.96 out of 5 average rating, 426 reviews
Guest favourite
Flat in Portland
Hip & Cozy, high end Modern Design
13–20 Nov
$165 SGD per night
4.9 out of 5 average rating, 341 reviews
Guest favourite
Guest suite in Portland
Gorgeous Studio 2 Blocks from Eastern Prom!
21–28 Oct
$155 SGD per night
4.91 out of 5 average rating, 193 reviews
Guest favourite
Guest house in Boothbay Harbor
The Sparrow’s Nest Charming Country Cottage
17–24 Sep
$507 SGD per night
5.0 out of 5 average rating, 225 reviews
Guest favourite
Flat in Portland
Munjoy Hill, East End 1 BR Portland, ME
6–13 Apr
$130 SGD per night
4.97 out of 5 average rating, 351 reviews
Guest favourite
Flat in Portland
Walk-able Portland Studio
11–18 Dec
$166 SGD per night
4.82 out of 5 average rating, 426 reviews
Guest favourite
Flat in Portland
Beautiful Apt in Historic Building - Old Port
30 Apr – 7 May
$289 SGD per night
4.94 out of 5 average rating, 384 reviews
Guest favourite
Flat in Portland
Small cozy downtown loft
12–19 Nov
$164 SGD per night
4.91 out of 5 average rating, 285 reviews
Guest favourite
Tiny home in Portland
The Garden Cabin Tiny Home
19–26 May
$173 SGD per night
4.97 out of 5 average rating, 397 reviews
Guest favourite
Flat in Portland
Charming Munjoy Hill Apartment
19–26 Mar
$127 SGD per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Portland
Harborview - Curated East End Escape w/ Parking
6–13 Apr
$412 SGD per night
5.0 out of 5 average rating, 35 reviews

Quick stats about holiday rentals in Portland

Total rentals

1.5K properties

Rentals with dedicated workspaces

770 properties have a dedicated workspace

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

390 properties allow pets

Family-friendly rentals

780 properties are a good fit for families

Total number of reviews

151K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Portland