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Search results; Over 1,000 homes in Portland

Top guest favourite
Flat in Portland
Private West End barn in walkable neighborhood
1 bedroom, 1 bed, 1 private bathroom
19–24 Oct
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4.99 out of 5 average rating, 424 reviews
Guest favourite
Room in South Portland
HomeAwhile - Extended Stay Suites
2 beds, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 165 reviews
Top guest favourite
Treehouse in Pownal
The Copper Fox Treehouse
1 bedroom, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.99 out of 5 average rating, 185 reviews
Guest favourite
Flat in Portland
Two Bedroom Loft at Boyd Block
2 bedrooms, 2 king beds, 2 bathrooms
27 Aug – 1 Sept
4.91 out of 5 average rating, 47 reviews
Top guest favourite
Tiny home in Scarborough
Cozy Tiny Cottage • 9mi Portland • 6mi Beach
1 bedroom, 2 beds, 1 bathroom
25–30 Aug
4.98 out of 5 average rating, 128 reviews
Top guest favourite
Cabin in Freeport
The Maine Frame | Modern A-Frame Cabin in Freeport
2 bedrooms, 2 beds, 1 bathroom
14–19 Nov
5.0 out of 5 average rating, 144 reviews
Camper van/Motorhome in Portland
Modern Camper Retreat Near Portland Jetport (PWM)
1 bed, WC
5–10 Aug
New place to stay
Guest favourite
Townhouse in Portland
Elegant & spacious 2-bedroom, 1.5-bath townhouse
2 bedrooms, 2 beds, 1.5 bathrooms
8–13 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds, 3 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 51 reviews
Home in Kennebunk
Private, family friendly getaway.
3 bedrooms, 8 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Portland
A quintessential Portland getaway.
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Home in Portland
Walton Home
3 bedrooms, 3 beds, 1 bathroom
9–14 Aug
New place to stay
Top guest favourite
Flat in Portland
Adorable getaway on the Eastern Promenade
1 bedroom, 2 beds, 1 bathroom
13–18 Nov
4.93 out of 5 average rating, 696 reviews
Top guest favourite
Tiny home in Scarborough
Southern Maine Tiny Home Cottage
1 bedroom, 2 beds, 1 bathroom
25–30 Sept
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Portland
Sunny 2-bedroom in Portland, ME
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 84 reviews
Top guest favourite
Cottage in Pownal
Dreamy Post&Beam Hideaway Near Portland & Freeport
1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
4.99 out of 5 average rating, 470 reviews
Guest house in Falmouth
Charming Guest House in the heart of Falmouth
1 bedroom, 2 queen beds, 1 bathroom
5–10 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Portland
Modern Retreat in East Bayside - walk to it all!
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Flat in Portland
Old Port Loft - 302
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 24 reviews