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Search results; Over 1,000 homes in Portland

Top guest favourite
Apartment in Portland
Walk to Top Dining • Boutique Stay • Parking
2 bedrooms, 1 bed, 1.5 private bathrooms
29 Oct – 3 Nov
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4.99 out of 5 average rating, 175 reviews
Top guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms, 5 beds, 1.5 bathrooms
18–23 Oct
4.96 out of 5 average rating, 177 reviews
Guest favourite
Hotel room in Portland
Steps to Old Port | Hostel Bed in 8-Bed Coed Dorm
1 bedroom, 4 bunk beds, 3.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 229 reviews
Top guest favourite
Flat in Portland
1-bedroom unit (3 beds) with free parking
1 bedroom, 3 beds, 1 bathroom
1–6 Nov
4.95 out of 5 average rating, 151 reviews
Top guest favourite
Home in Portland
Top Deck - Portland Property with Views!
3 bedrooms, 10 beds, 2.5 bathrooms
25–30 Oct
4.92 out of 5 average rating, 304 reviews
Cottage in Portland
Cozy Renovated Home | Portland, ME
2 bedrooms, 2 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 4 reviews
Home in Portland
Lock's Nest on Peaks Island Maine
3 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms, 3 beds, 1 bathroom
7–12 Nov
5.0 out of 5 average rating, 27 reviews
Guest favourite
Flat in Portland
Back Cove Retreat | Walk, Relax, Explore
2 bedrooms, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest house in Portland
Spacious & Convenient 2 Bd/1 bath w/ Free Parking
2 bedrooms, 3 beds, 1 bathroom
30 Oct – 4 Nov
4.96 out of 5 average rating, 522 reviews
Top guest favourite
Home in Cape Elizabeth
"Periwinkle" ~ a Charming Oceanfront Cottage
3 bedrooms, 3 beds, 1.5 bathrooms
1–7 Apr
5.0 out of 5 average rating, 39 reviews
Superhost
Flat in South Portland
The Perch at Willard Square-Elegant Beach Getaway
2 bedrooms, 3 beds, 1 bathroom
4–9 Oct
New place to stay
Top guest favourite
Cabin in Freeport
Chickadee A-Frame
3 bedrooms, 3 beds, 2 bathrooms
25–30 Sept
4.98 out of 5 average rating, 88 reviews
Top guest favourite
Flat in Portland
Boutique BnB in The Heart of East End Portland!
2 bedrooms, 3 beds, 1 bathroom
30 Oct – 4 Nov
4.98 out of 5 average rating, 486 reviews
Flat in Portland
Charming Victorian Home • West End • Parking
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Portland
The Howard on Munjoy Hill
1 bedroom, 1 queen bed, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 229 reviews
Top guest favourite
Home in Portland
Wall St. Retreat: Family-Ready Portland Home
3 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Portland
Harborview - Curated East End Escape w/ Parking
2 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.99 out of 5 average rating, 154 reviews
Top guest favourite
Flat in Portland
Old Port Loft -400
4 bedrooms, 5 beds, 3 bathrooms
3–8 Oct
4.96 out of 5 average rating, 57 reviews