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Search results; Over 1,000 homes in Portland

Top guest favourite
Home in Portland
Top Deck - Portland Property with Views!
3 bedrooms, 10 beds, 2.5 shared bathrooms
30 Aug – 4 Sept
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4.92 out of 5 average rating, 296 reviews
Guest favourite
Room in South Portland
HomeAwhile - Extended Stay Suites
4.93 out of 5 average rating, 137 reviews, 2 beds, 1 bathroom
14–19 Aug
Top guest favourite
Cabin in Freeport
The Maine Frame | Modern A-Frame Cabin in Freeport
5.0 out of 5 average rating, 139 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Nov
Home in Portland
Walton Home
New place to stay, 3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Flat in Portland
A quintessential Portland getaway.
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
Top guest favourite
Flat in Portland
The Yankee Dugout
4.98 out of 5 average rating, 191 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Top guest favourite
Flat in Portland
Large Sunny Apartment Near Downtown/Arts District
4.96 out of 5 average rating, 475 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Nov
Top guest favourite
Home in Portland
Wall St. Retreat: Family-Ready Portland Home
5.0 out of 5 average rating, 20 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
Top guest favourite
Apartment in Portland
Charming 2-Bedroom Back Cove Retreat
4.98 out of 5 average rating, 96 reviews, 2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
Top guest favourite
Treehouse in Pownal
The Copper Fox Treehouse
4.99 out of 5 average rating, 180 reviews, 1 bedroom, 3 beds, 1 bathroom
26–31 Aug
Top guest favourite
Home in Falmouth
The little blue cottage
5.0 out of 5 average rating, 6 reviews, 2 beds, 1 bathroom
8–13 Sept
Top guest favourite
Flat in Portland
Charming West End Victorian
4.95 out of 5 average rating, 450 reviews, 1 bedroom, 3 beds, 1 bathroom
31 Oct – 5 Nov
Home in Westbrook
Cozy Cape in the Brook
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
Top guest favourite
Cabin in Freeport
Glamping cabin w/ kitchenette & full bath - 17
5.0 out of 5 average rating, 56 reviews, 1 bedroom, 2 beds, 1 bathroom
22–27 Aug
Top guest favourite
Home in Portland
East End Unit
4.94 out of 5 average rating, 177 reviews, 1 bedroom, 2 beds, 1 bathroom
8–13 Nov
Top guest favourite
Flat in Portland
Cozy East End 2 Bdrm. with Private Entrance
4.97 out of 5 average rating, 578 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Flat in Portland
Quiet Comfy Victorian Escape
4.97 out of 5 average rating, 214 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
Home in Portland
Charming house near downtown and comfortable.
New place to stay, 3 bedrooms, 3 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Flat in South Portland
Second floor 3BR/2BA Near Willard Beach & Portland
4.92 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Oct