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Search results; Over 1,000 homes in Portland

Top guest favourite
Flat in Portland
Old Port Penthouse Suite - Amazing Harbor Views
2 bedrooms, 2 beds, 2 private bathrooms
26–31 Oct
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4.97 out of 5 average rating, 323 reviews
Superhost
Room in South Portland
HomeAwhile - Extended Stay Suites
2 beds
23–28 Aug
4.92 out of 5 average rating, 165 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
Treehouse in Pownal
The Copper Fox Treehouse
1 bedroom, 3 beds
18–23 Oct
4.99 out of 5 average rating, 186 reviews
Top guest favourite
Home in Freeport
Mermaid's Chair | Private Beach | Hot Tub
2 bedrooms, 2 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Guest house in Saco
Brand-New Private Studio with Large Balcony – Saco
1 bedroom, 2 beds
26–31 Oct
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Loft in Portland
Sunny Arts Dist. Studio- Queen Bed & FREE Parking
2 beds
25–30 Oct
4.94 out of 5 average rating, 795 reviews
Guest favourite
Guest suite in Portland
Large, spacious, and eclectic Room, Private Bath
1 bedroom, 1 queen bed
26–31 Oct
4.89 out of 5 average rating, 746 reviews
Top guest favourite
Flat in Portland
Quiet Comfy Victorian Escape
2 bedrooms, 2 queen beds
2–7 Nov
4.97 out of 5 average rating, 216 reviews
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds
28 Oct – 2 Nov
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Tiny home in Scarborough
Southern Maine Tiny Home Cottage
1 bedroom, 2 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Tiny home in Freeport
Cozy Rock Cabin #thewaylifeshouldbe
2 bedrooms, 2 beds
28 Aug – 2 Sept
4.99 out of 5 average rating, 386 reviews
Guest favourite
Flat in Portland
Adorable getaway on the Eastern Promenade
1 bedroom, 2 beds
13–18 Nov
4.93 out of 5 average rating, 698 reviews
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, 129 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
Top guest favourite
Guest house in Portland
Spacious & Convenient 2 Bd/1 bath w/ Free Parking
2 bedrooms, 3 beds
20–25 Sept
4.96 out of 5 average rating, 520 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
Apartment in Portland
Mary J. Eastburn House - Baxter Suite
1 bedroom, 2 beds
9–14 Aug
5.0 out of 5 average rating, 147 reviews
Top guest favourite
Flat in Portland
Large Sunny Apartment Near Downtown/Arts District
1 bedroom, 1 queen bed
20–25 Nov
4.96 out of 5 average rating, 479 reviews