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Search results; Over 1,000 homes in Middletown

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Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #202
1 queen bed
27 Sept – 2 Oct
4.95 out of 5 average rating, 39 reviews
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Guest favourite
Room in Middletown
Charming Upstate New York Inn Cozy Suite #203
2 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Middletown
Peace and quiet. Comfy, private house to relax in
4 bedrooms, 4 beds
9–14 Nov
4.98 out of 5 average rating, 224 reviews
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Top guest favourite
Home in Middletown
Industrial Modern Home - 360 Views!
4 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 21 reviews
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Home in Otisville
3BedRM Cozy Home Otisville Middletown Deer Park
3 bedrooms, 3 beds
20–25 Sept
4.71 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Chester
4 Bedroom Home with Hot-Tub
4 bedrooms, 8 beds
19–25 Oct
5.0 out of 5 average rating, 59 reviews
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Top guest favourite
Home in Middletown
Private Secret Escape • Hot Tub • Pool • Fire Pit
4 bedrooms, 8 beds
25–30 Oct
5.0 out of 5 average rating, 5 reviews
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Luxe
Villa in Middletown
Pinnacle Pointe | Year-Round Pool Spa Lake Theater
7 bedrooms, 12 beds
5–10 Oct
4.92 out of 5 average rating, 12 reviews
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Guest favourite
Flat in Chester
Luxury Apt/Sugar Loaf/10 Min To LEGOLAND
2 bedrooms, 3 beds
1–6 Nov
4.96 out of 5 average rating, 435 reviews
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Top guest favourite
Home in Middletown
5Bdrm Estate/Tennis near LegoLand
5 bedrooms, 7 beds
21–26 Sept
4.97 out of 5 average rating, 72 reviews
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Top guest favourite
Cottage in Florida
Fall Fun, Apple Picking, Wineries & LegoLand!
3 bedrooms, 4 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 69 reviews
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Top guest favourite
Villa in Goshen
Spectacular Historic Mansion w/Pool&Tennis
10 bedrooms, 17 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 43 reviews
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Home in Montgomery
Cozy Montgomery Home
2 bedrooms, 2 beds
1–6 Dec
New place to stay
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Guest favourite
Guest suite in Montgomery
the Guest Suite at Dunhill Pond
1 bedroom, 1 king bed
20–25 Sept
4.88 out of 5 average rating, 57 reviews
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Top guest favourite
Cottage in Goshen
Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND
2 bedrooms, 2 beds
11–16 Nov
4.92 out of 5 average rating, 349 reviews
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Top guest favourite
Home in Montgomery
Fairway Retreat - Montgomery, NY
6 bedrooms, 9 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 44 reviews
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Guest favourite
Villa in Bloomingburg
Spacious 6BR Villa | Serene Scenic Mountain Escape
6 bedrooms, 11 beds
20–25 Sept
4.87 out of 5 average rating, 117 reviews
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Guest favourite
Cabin in Sussex
Near Mt Creek, Lake Glenwood, Crystal Cabin-Vernon
2 bedrooms, 2 queen beds
20–25 Sept
4.91 out of 5 average rating, 113 reviews