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Roxbury Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Roxbury Vacation Homes

Cozy year round retreat! Close to skiing, hiking and swimming.
Relax on the covered deck with Adirondack chairs, a table, and a grill for outdoor cooking.

Cozy year round retreat! Close to skiing, hiking and swimming.

10.0 out of 10, Exceptional, (48)
"Summer in the Catskills is a treat and these are the accommodations to enjoy it to its fullest. Can’t wait to stay again!"
Cozy year round retreat! Close to skiing, hiking and swimming.
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Relax on the deck with Adirondack chairs overlooking a serene landscape.

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

9.0 out of 10, Wonderful, (48)
"Great for in town stays"
The price is CA $155
CA $277 total
includes taxes & fees
Aug 11 - Aug 12
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Beautiful, private Property/swimming pond
Enjoy meals in this inviting dining area with a large table and comfortable chairs.

Beautiful, private Property/swimming pond

9.6 out of 10, Exceptional, (72)
"We had an amazing stay at this home during our family ski trip. The house was spacious, clean, and perfectly located near the slopes. The host was responsive and made sure we had everything we needed. We would definitely stay here again—highly recommend for a relaxing and fun ski getaway."
Beautiful, private Property/swimming pond
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
Relax in a serene outdoor hot tub area surrounded by trees and a deck.

Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

9.8 out of 10, Exceptional, (78)
"Location is great; close to a lot of hiking opportunities and right in the middle of breathtaking scenery. The house was clean and provided excellent accomodations."
The price is CA $557
CA $972 total
includes taxes & fees
Aug 10 - Aug 11
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, gas stove, and wooden cabinets.

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

2.0 star property
8.8 out of 10, Excellent, (17)
"Thank you so much for an amazing stay"
The price is CA $206
CA $475 total
includes taxes & fees
Aug 12 - Aug 13
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub
Enjoy cooking in this kitchen with a large window offering a view of the outside, featuring a stove, kettle, coffee maker, and dishwasher.

Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

9.8 out of 10, Exceptional, (75)
"Very relaxing, well equipped home. Hot tub was fantastic. Kitchen fully stocked with pots, pans, cooking and eating utensils. "
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub
Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay
Relax in a serene outdoor setting surrounded by a mature tree and beautifully manicured lawn.

Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay

9.6 out of 10, Exceptional, (76)
"House was very clean. Property managers were very responsive to check in and check out time and anything we needed during our stay. Very close to the mountain and beautiful location. Would highly recommend."
Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay
The Catskills Red Barn-near Belleayre
Set amidst a serene forest, this charming archway offers a glimpse into a tranquil retreat.

The Catskills Red Barn-near Belleayre

10.0 out of 10, Exceptional, (45)
"Blythe is super helpful. We had a fantastic night in the cabin, which had so much character. Belleayre is so close, it’s a great little getaway to go and have some fun. "
The Catskills Red Barn-near Belleayre
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Relax in a hot tub on a spacious deck with stairs leading to a covered area.

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

4.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent house, very clean and great location. Host Henry was phenomenal at communicating and very helpful with any questions. Will definitely stay again."
The price is CA $179
CA $559 total
includes taxes & fees
Sep 9 - Sep 10
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Beautiful new house 3/4 mile from Hunter Mountain
Cozy cabin with a central entrance and windows on either side, set amidst a serene winter landscape.

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (130)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
Enjoy cooking in this well-lit kitchen with a large window and modern appliances.

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.8 out of 10, Exceptional, (46)
"The perfect family getaway"
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Enjoy cooking in this well-equipped kitchen with a dining area nearby.

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

9.4 out of 10, Exceptional, (50)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Country Home with Private Swimming Pond and Beautiful Mountain Views
Enjoy a serene lake view from this outdoor deck, complete with a table, chairs, and barbecue grill.

Country Home with Private Swimming Pond and Beautiful Mountain Views

10.0 out of 10, Exceptional, (116)
"The view is absolutely stunning! "
Country Home with Private Swimming Pond and Beautiful Mountain Views
A world where time stands still, close to Belleayre Ski & Wedding venues.
Enjoy cooking in this well-equipped kitchen with a large island and views of the surrounding greenery.

A world where time stands still, close to Belleayre Ski & Wedding venues.

9.6 out of 10, Exceptional, (18)
"We had the perfect weekend getaway—quiet, serene and comfy. The house was beautifully furnished and the outdoor space gave incredible views of the landscape. Highly recommend!"
The price is CA $246
CA $728 total
includes taxes & fees
Aug 18 - Aug 19
A world where time stands still, close to Belleayre Ski & Wedding venues.
Private Lakeside Retreat 'Away from it All!'
Cozy living space with a kitchenette, sofa, dining table, and shelves.

Private Lakeside Retreat 'Away from it All!'

10.0 out of 10, Exceptional, (21)
"Great laid back stay, we rarely left."
Private Lakeside Retreat 'Away from it All!'
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
Cozy living area with a sofa, coffee table, and dining table for four, surrounded by framed pictures and natural wood accents.

Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace

10.0 out of 10, Exceptional, (43)
"Excellent log cabin home, perfect home base for a ski weekend at Windham. "
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
2025 Log Home- Ski Chalet w/ Luxury Amenities. direct Views of Hunter Slopes
Exterior

2025 Log Home- Ski Chalet w/ Luxury Amenities. direct Views of Hunter Slopes

2025 Log Home- Ski Chalet w/ Luxury Amenities. direct Views of Hunter Slopes
Home for all Seasons in Margaretville, New York
Relax in this serene outdoor seating area with a brick wall backdrop, featuring two comfortable chairs and a small table.

Home for all Seasons in Margaretville, New York

9.6 out of 10, Exceptional, (10)
"House was clean and in a good location. We enjoyed our stay. "
Home for all Seasons in Margaretville, New York
Blackbear Lodge - Luxury Cabin, Kid-Friendly
Relax in this inviting living space with a comfortable sofa, exposed wooden beams, and a cozy fireplace.

Blackbear Lodge - Luxury Cabin, Kid-Friendly

10.0 out of 10, Exceptional, (4)
"We had a great stay here! Everything was comfortable and just all around easy. The location is amazing—we loved that it's tucked away and private without being so out of the way. "
Blackbear Lodge - Luxury Cabin, Kid-Friendly
New Luxuary Hunter Ski Resort&Lake Chalet, Hot Tub, Sauna, Fireplace, Mountains
Enjoy a serene lake view from the deck, surrounded by trees and distant hills.

New Luxuary Hunter Ski Resort&Lake Chalet, Hot Tub, Sauna, Fireplace, Mountains

10.0 out of 10, Exceptional, (9)
"Tons of activities in house beautiful area."
The price is CA $898
CA $1,589 total
includes taxes & fees
Aug 20 - Aug 21
New Luxuary Hunter Ski Resort&Lake Chalet, Hot Tub, Sauna, Fireplace, Mountains
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Roxbury Hotel Reviews

The Colonial Motel

The Colonial Motel

10/10 Excellent
"First time in NY and loved this stay. Even though it was one night I slept like a baby. Favorite thing was the confortable bed and pillows. Absolutely loved the sheets and cover. Truly felt at home. Plus Josh, was very friendly and made us feel really welcomed! "
Adriele 1-night trip
Posted 18 hours ago
The Colonial Motel