We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Preston Hollow Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighborhood
50 rentals in Preston Hollow.
Sort by:
Tripadvisor Sort
Tentrr Signature Site - Creekside Zen in Catskills
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Great 5 BR House !!!!
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain
9 bedrooms
5 bathrooms
Sleeps 30
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Windham Log Cabin on 35 Acres
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Winsome Windham - Secluded Chalet with Ski Windham Views
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Spacious Retreat with Luxurious View
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
'New Home' Idyllic Mt Views ,Pond & Horse farm views 2 min to Town
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Preston Hollow rentals sent straight to your email!
Beautiful Home, Gorgeous View, Spacious Living
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The perfect mountain getaway nestled in the woods 2 min from downtown Windham.
4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Mountain House Retreat
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cozy Log Cabin
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
FAB FUN GREEN BUILT FARMHOUSE ON 17 ACRES
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!
12 bedrooms
10 bathrooms
Sleeps 33
Match: Sleeps
More info
Check in
Check out
Payment Protection
Secluded Charming Water Front Log Home
4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
More info
Check in
Check out
Payment Protection
Year-Round Relaxing Mountain Escape
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
WINDHAM MAGNIFICENT HOLIDAY GETAWAY
5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
More info
Check in
Check out
Payment Protection
Spacious Mountain Escape - Minutes to Windham/Hunter
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Historic Catskill Mountain House close to Windham
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
Payment Protection
Armstrongs Elk Farm
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Mountain House: The Perfect 4 Season Retreat
8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
More info
Check in
Check out
Payment Protection
Mountain views and seclusion in a rustic midcentury home on Catskill Creek.
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Lakefront Windham Area Home w/ Pool, Boat & Dock!
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Meadows, Birdsong, Peace and Quiet
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Xenia
4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Payment Protection
Rare Ski Mountain View!
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Modern Home w/ Deck, 5 Minutes to Windham Resort!
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - Bearkill Brook
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - Creekside Thyme
1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - Renew Yourself Renew the Earth
1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - Sacred Hollow
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Country Place Resort Home of Zoom Flume Water park
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Chateau Tina Tiny Luxury Cabin Sleeps 6 Dog Friendly
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
VILLA MARIE Luxury Cabin from our Tiny Cabin Collection Dogs ok
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cozy Cabin Sleeps 2 Dog Friendly
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Windham Mtn Home w/Deck & BBQ: ~3 Mi to Zoom Flume
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - Moon Song Farm
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Garden Room Suite at the Van Winkle Inn
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Payment Protection
Turner Suite
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Peggy Madeline Suite at the Van Winkle Inn
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Castle Family Suite
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Hannah Suite at the Van Winkle Inn
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
NEW! High Peak Heaven: Cozy Log Cabin on 1 Acre!
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Catskill Mtn Home w/Deck, 1.2Mi to Zoom Flume
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
NEW! Home w/Sauna & Fire Pit, 13 Mi to Windham Mtn
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Updated Catskills Mtn. Retreat w/ Panoramic Views!
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Luxury Home w/ Deck: Explore the Catskill Mtns!
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
PreviousNext
1