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Search results; Over 1,000 homes in Portland

Top guest favourite
Home in Portland
Explore Portland from a 18th-Century Victorian
1 bedroom, 1 bed, 1 private bathroom
13–18 Jul
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4.96 out of 5 average rating, 369 reviews
Flat in Portland
Studio on Old Farm
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
New place to stay
Top guest favourite
Room in Freeport
Freeport, Maine
1 queen bed, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 267 reviews
Top guest favourite
Yurt in Windham
Sebago Sunrise Yurt - Trail Access!
1 bedroom, 1 queen bed, Toilet with sink
21–26 Jun
4.98 out of 5 average rating, 117 reviews
Top guest favourite
Treehouse in Pownal
The Copper Fox Treehouse
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 171 reviews
Guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 346 reviews
Guest favourite
Flat in Portland
Cozy Two Bedroom West End
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Jun
5.0 out of 5 average rating, 6 reviews
Home in Old Orchard Beach
Entire home in Old Orchard Beach
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
New place to stay
Guest favourite
Flat in Portland
Modern Studio Loft w/ Parking in Perfect Location
1 queen bed, 1 bathroom
25–30 Oct
4.95 out of 5 average rating, 760 reviews
Guest favourite
Home in Naples
LUX Designer Private Waterfront Hot Tub - Secluded
1 king bed, 1 bathroom
21–26 Jun
4.98 out of 5 average rating, 187 reviews
Top guest favourite
Flat in Portland
Thompson's Point Studio
1 bedroom, 1 queen bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 101 reviews
Top guest favourite
Flat in Portland
Cozy East End 2 Bdrm. with Private Entrance
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 568 reviews
Top guest favourite
Flat in Portland
Quiet Comfy Victorian Escape
2 bedrooms, 2 queen beds, 1 bathroom
17–22 Oct
4.97 out of 5 average rating, 209 reviews
Guest favourite
Flat in Portland
Historic + Modern, Sun Filled West End 1BR Apt.
1 bedroom, 1 queen bed, 1 bathroom
4–9 Nov
4.88 out of 5 average rating, 352 reviews
Top guest favourite
Room in Falmouth
Green Room at Foreside Farmhouse
1 bed, 1.5 bathrooms
28 Jun – 3 Jul
4.99 out of 5 average rating, 88 reviews
Top guest favourite
Place to stay in Portland
Carrabassett Lodge
2 bedrooms, 3 beds, 1 bathroom
2–7 Sept
5.0 out of 5 average rating, 130 reviews
Superhost
Bed and breakfast in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
1 bedroom, 1 bed, 1 bathroom
14–19 Jul
Top guest favourite
Cottage in Pownal
Dreamy Post&Beam Hideaway Near Portland & Freeport
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.99 out of 5 average rating, 458 reviews
Top guest favourite
Apartment in Portland
Mary J. Eastburn House--Mountain View Suite
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Jun
4.97 out of 5 average rating, 109 reviews