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Search results; Over 1,000 homes in Portland

Guest favourite
Room in South Portland
HomeAwhile - Extended Stay Suites
2 beds
16–21 Aug
4.92 out of 5 average rating, 165 reviews
Guest favourite
Flat in Portland
Two Bedroom Loft at Boyd Block
2 bedrooms, 2 king beds
27 Aug – 1 Sept
4.91 out of 5 average rating, 47 reviews
Top guest favourite
Treehouse in Pownal
The Copper Fox Treehouse
1 bedroom, 3 beds
28 Aug – 2 Sept
4.99 out of 5 average rating, 185 reviews
Top guest favourite
Cabin in Freeport
The Maine Frame | Modern A-Frame Cabin in Freeport
2 bedrooms, 2 beds
14–19 Nov
5.0 out of 5 average rating, 144 reviews
Top guest favourite
Home in Old Orchard Beach
Luxury Home w/HOT TUB & Fire Pit
3 bedrooms, 3 beds
25–30 Oct
4.96 out of 5 average rating, 226 reviews
Camper van/Motorhome in Portland
Modern Camper Retreat Near Portland Jetport (PWM)
1 bed
6–11 Aug
New place to stay
Top guest favourite
Tiny home in Scarborough
Cozy Tiny Cottage • 9mi Portland • 6mi Beach
1 bedroom, 2 beds
25–30 Aug
4.98 out of 5 average rating, 128 reviews
Top guest favourite
Flat in Portland
The Yankee Dugout
2 bedrooms, 3 beds
30 Aug – 4 Sept
4.98 out of 5 average rating, 196 reviews
Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Tiny home in Scarborough
Southern Maine Tiny Home Cottage
1 bedroom, 2 beds
25–30 Sept
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Portland
Old Port Loft - 302
1 bedroom, 2 beds
16–21 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Flat in Portland
A quintessential Portland getaway.
2 bedrooms, 2 beds
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Pownal
Dreamy Post&Beam Hideaway Near Portland & Freeport
1 bedroom, 2 beds
31 Aug – 5 Sept
4.99 out of 5 average rating, 470 reviews
Hotel room in Portland
Chic Comfort w/ Waterfront Views – Old District
1 bedroom, 2 queen beds
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Portland
Mary J. Eastburn House - Baxter Suite
1 bedroom, 2 beds
9–14 Aug
5.0 out of 5 average rating, 146 reviews
Top guest favourite
Home in Portland
East End Unit
1 bedroom, 2 beds
7–12 Nov
4.94 out of 5 average rating, 182 reviews
Guest favourite
Room in Falmouth
Green Room at Foreside Farmhouse
1 bed
30 Aug – 4 Sept
4.96 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Portland
Chic Portland Penthouse, 2BR
2 bedrooms, 2 beds
23–28 Aug
4.98 out of 5 average rating, 150 reviews