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Search results; Over 1,000 homes in Portland
Over 1,000 homes in Portland
Top guest favourite
Guest favourite
Cottage in Portland
Classic Peaks Island Cottage - 5 min walk to Ferry
3 bedrooms
,
·
4 beds
,
·
1 private bathroom
20–25 Sept
20–25 Sept
$4,108 SGD
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for 5 nights
$4,108 SGD for 5 nights
,
·
5.0 out of 5 average rating, 74 reviews
5.0 (74)
Top guest favourite
Guest favourite
Home in Portland
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
12–17 Oct
12–17 Oct
$3,985 SGD
$3,611 SGD
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for 5 nights
Book early to save
Free cancellation
4.97 out of 5 average rating, 175 reviews
4.97 (175)
Top guest favourite
Guest favourite
Home in Portland
Modern Portland House - Minutes to the Old Port!
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
7–12 Sept
7–12 Sept
$2,924 SGD
$2,642 SGD
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for 5 nights
5.0 out of 5 average rating, 16 reviews
5.0 (16)
Top guest favourite
Guest favourite
Flat in South Portland
2 bedroom, 1 bath of coastal comfort & airy charm
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
7–12 Nov
7–12 Nov
$1,569 SGD
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for 5 nights
$1,569 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 24 reviews
5.0 (24)
Guest favourite
Guest favourite
Flat in Portland
Lovely 4 Bedroom with free parking
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
20–25 Sept
20–25 Sept
$3,715 SGD
$1,976 SGD
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for 5 nights
4.86 out of 5 average rating, 205 reviews
4.86 (205)
Guest favourite
Guest favourite
Holiday home in Portland
Heron's Perch on Peaks' Island
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
20–25 Sept
20–25 Sept
$5,455 SGD
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for 5 nights
$5,455 SGD for 5 nights
4.95 out of 5 average rating, 42 reviews
4.95 (42)
Top guest favourite
Guest favourite
Flat in South Portland
Stylish New Apartment Near Willard Beach w/ Yard
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
20–25 Sept
20–25 Sept
$4,943 SGD
$3,721 SGD
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for 5 nights
4.99 out of 5 average rating, 85 reviews
4.99 (85)
Top guest favourite
Guest favourite
Cottage in Harpswell
Updated 1890s Cottage, Private Waterfront, Firepit
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
9–14 Sept
9–14 Sept
$6,520 SGD
$4,815 SGD
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for 5 nights
5.0 out of 5 average rating, 17 reviews
5.0 (17)
Guest favourite
Guest favourite
Home in Portland
Charming house near downtown and comfortable.
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
4–9 Oct
4–9 Oct
$2,307 SGD
$2,028 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Apartment in Portland
First Floor Portland Condo 3 Bed 2 Bath + Parking
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
20–25 Oct
20–25 Oct
$3,139 SGD
$2,480 SGD
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for 5 nights
Free cancellation
4.96 out of 5 average rating, 375 reviews
4.96 (375)
Guest favourite
Guest favourite
Flat in Portland
1875 West End Victorian | EV Charging + Parking
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
9–14 Nov
9–14 Nov
$1,325 SGD
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for 5 nights
$1,325 SGD for 5 nights
4.81 out of 5 average rating, 738 reviews
4.81 (738)
Top guest favourite
Guest favourite
Home in Windham
Lakehouse on Highland Lake
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
26–31 Oct
26–31 Oct
$2,748 SGD
$2,475 SGD
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for 5 nights
Free cancellation
4.97 out of 5 average rating, 89 reviews
4.97 (89)
Top guest favourite
Guest favourite
Flat in Portland
2 Floor 4 Bed/2 Bath Unit STHR0037112021
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
7–12 Sept
7–12 Sept
$4,908 SGD
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for 5 nights
$4,908 SGD for 5 nights
5.0 out of 5 average rating, 88 reviews
5.0 (88)
Top guest favourite
Guest favourite
Flat in Portland
Quiet Comfy Victorian Escape
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
2–7 Nov
2–7 Nov
$1,792 SGD
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for 5 nights
$1,792 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 223 reviews
4.96 (223)
Top guest favourite
Guest favourite
Flat in Portland
Harborview - Curated East End Escape w/ Parking
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
25–30 Oct
25–30 Oct
$3,642 SGD
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for 5 nights
$3,642 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 154 reviews
4.99 (154)
Guest favourite
Guest favourite
Home in Falmouth
Large Historic 7 Bedroom home with Pool & Hot Tub
7 bedrooms
7 bedrooms
,
·
10 beds
10 beds
27 Sept – 2 Oct
27 Sept – 2 Oct
$12,296 SGD
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for 5 nights
$12,296 SGD for 5 nights
4.88 out of 5 average rating, 118 reviews
4.88 (118)
Top guest favourite
Guest favourite
Cottage in Portland
4br2ba House+parking@PeacefulOasis on Munjoy Hill
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
30 Nov – 5 Dec
30 Nov – 5 Dec
$2,427 SGD
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for 5 nights
$2,427 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 302 reviews
4.97 (302)
Guest favourite
Guest favourite
Home in Portland
Stunning Ocean Views From This Peaks Island Home
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
27 Oct – 1 Nov
27 Oct – 1 Nov
$2,529 SGD
$2,211 SGD
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for 5 nights
4.9 out of 5 average rating, 123 reviews
4.9 (123)
Guest favourite
Guest favourite
Guest suite in Portland
Large, spacious, and eclectic Room, Private Bath
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
26–31 Oct
26–31 Oct
$742 SGD
$668 SGD
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for 5 nights
Free cancellation
4.89 out of 5 average rating, 759 reviews
4.89 (759)
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