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Search results; Over 1,000 homes in Portland

Guest favourite
Boutique hotel in Portland
The Library | Guestroom 6
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
,
4.97 out of 5 average rating, 74 reviews
Guest favourite
Hotel in South Portland
HomeAwhile - Extended Stay Suites
4.93 out of 5 average rating, 137 reviews, 1 bedroom, 2 beds, No bathroom
12–17 Jul
Top guest favourite
Cabin in Freeport
Cozy, secluded geodesic dome - 27
4.93 out of 5 average rating, 56 reviews, 1 bedroom, 1 bed, No bathroom
10–15 Aug
Guest favourite
Flat in Portland
Modern Studio Loft w/ Parking in Perfect Location
4.95 out of 5 average rating, 770 reviews, 1 bed, 1 bathroom
25–30 Oct
Guest favourite
Guest house in Saco
Brand-New Private Studio with Large Balcony – Saco
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 Sept
Top guest favourite
Tiny home in Portland
The Garden Cabin Tiny Home
4.95 out of 5 average rating, 537 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Dec
Top guest favourite
Room in Biddeford
King Bedroom at Thistle Pond. Close to UNE & Beach
5.0 out of 5 average rating, 60 reviews, 1 king bed, 1 bathroom
2–7 Aug
Top guest favourite
Guest house in Yarmouth
Private Guesthouse in the Woods
4.99 out of 5 average rating, 204 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Oct
Top guest favourite
Flat in Portland
Old Port Loft - 302
5.0 out of 5 average rating, 23 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Portland
RETRO BnB in the Heart of East End Portland
4.96 out of 5 average rating, 555 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Oct
Boat in Portland
Stay Aboard Enchanted – Your Dockside Getaway
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 1 bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Portland
Explore Portland from a 18th-Century Victorian
4.95 out of 5 average rating, 371 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Flat in Portland
Quiet Comfy Victorian Escape
4.97 out of 5 average rating, 211 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Oct
Top guest favourite
Flat in Portland
Peaks Island Master Bedroom Suite
4.99 out of 5 average rating, 220 reviews, 1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Flat in Portland
The Howard on Munjoy Hill
4.98 out of 5 average rating, 210 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Room in Freeport
Freeport, Maine
4.96 out of 5 average rating, 273 reviews, 1 queen bed, 1 bathroom
17–22 Oct
Top guest favourite
Cottage in Pownal
Dreamy Post&Beam Hideaway Near Portland & Freeport
4.99 out of 5 average rating, 465 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Aug – 5 Sept
Guest favourite
Cabin in Freeport
Large, luxurious geodesic dome - 08
4.98 out of 5 average rating, 47 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Jul – 3 Aug
Superhost
Bed and breakfast in Portland
Aerie 2 reg:STHR-007375-2025 Peaks Island, Me
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept