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Search results; Over 1,000 homes in Portland

Guest favorite
Panoramic ocean views greet you at this Victorian third-floor Munjoy Hill apartment
1 bedroom, 1 bed, 1 private bath
Sep 7 – 12
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4.86 out of 5 average rating, 600 reviews
Top guest favorite
Soak in ocean views from every window at this oceanfront Cape Elizabeth cottage
5.0 out of 5 average rating, 35 reviews, 3 bedrooms, 3 beds, 1.5 baths
Nov 8 – 14
Top guest favorite
This East End apartment puts you a 4-minute walk from Casco Bay, with a private porch
4.93 out of 5 average rating, 698 reviews, 1 bedroom, 2 beds, 1 bath
Nov 13 – 18
Top guest favorite
Private room
Wake to Casco Bay harbor views at this Munjoy Hill 19th-century home
4.92 out of 5 average rating, 1240 reviews, 2 bedrooms, 2 beds, 1 bath
Nov 16 – 21
Top guest favorite
This hand-crafted fox-shaped Pownal treehouse puts you in the treetops
4.99 out of 5 average rating, 186 reviews, 1 bedroom, 3 beds, 1 bath
Sep 13 – 18
Top guest favorite
Light and airy Meeting House Hill apartment with a private backyard and hammock
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 28 – Nov 2
Top guest favorite
This brand-new Saco guesthouse gives you a 200 sq ft balcony over gardens and woods
5.0 out of 5 average rating, 17 reviews, 1 bedroom, 2 beds, 1 bath
Oct 26 – 31
Top guest favorite
Watch ferries from your private deck at this Old Port penthouse loft
4.97 out of 5 average rating, 318 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 22 – 27
Top guest favorite
Take in city views from the rooftop deck of this Old Port penthouse loft
4.96 out of 5 average rating, 54 reviews, 4 bedrooms, 5 beds, 3 baths
Aug 30 – Sep 4
Top guest favorite
Sip craft beers on your screened porch at this 128-sqft Portland tiny home
4.95 out of 5 average rating, 552 reviews, 1 bedroom, 1 bed, 1.5 baths
Dec 1 – 6
Guest favorite
Ocean views greet you at this Old Port loft in a historic 1900 building
4.95 out of 5 average rating, 61 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 4 – 9
Superhost
Room in South Portland
HomeAwhile - Extended Stay Suites
4.92 out of 5 average rating, 170 reviews, 2 beds, 1 bath
Aug 20 – 25
Top guest favorite
This artist-designed West End loft gives you harbor views from a private deck
4.94 out of 5 average rating, 339 reviews, 1 bedroom, 1 bed, 1 bath
Oct 24 – 29
This Kennebunk house gives you a heated pool, fire pit, and game room on 3 acres
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 8 beds, 2 baths
Oct 25 – 30
Top guest favorite
This newly built Scarborough tiny house gives you high ceilings and a fireplace
5.0 out of 5 average rating, 76 reviews, 1 bedroom, 2 beds, 1 bath
Oct 30 – Nov 4
Top guest favorite
This newly renovated Old Port loft puts you in the heart of Portland’s nightlife
5.0 out of 5 average rating, 25 reviews, 1 bedroom, 2 beds, 1 bath
Aug 16 – 21
Top guest favorite
This 150-year-old waterfront barn in Stroudwater gives you Fore River views
5.0 out of 5 average rating, 487 reviews, 1 bed, 1 bath
Oct 29 – Nov 3
Guest favorite
Wake to woods through the glass wall of this A-frame cabin in Pownal
4.93 out of 5 average rating, 189 reviews, 1 bedroom, 1 bed, No bathroom
Aug 16 – 21
Top guest favorite
Look out over Casco Bay from the private deck of this Munjoy Hill apartment
4.99 out of 5 average rating, 151 reviews, 2 bedrooms, 4 beds, 2 baths
Oct 25 – 30