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.

Oak Hill 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 Oak Hill.
Sort by:
Tripadvisor Sort
NEW! Home w/Sauna & Fire Pit, 13 Mi to Windham Mtn, vacation rental in Oak Hill

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
Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

*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, vacation rental in Oak Hill

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
Close to both Hunter and Windham Mnts, vacation rental in Oak Hill

Close to both Hunter and Windham Mnts

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
'New Home' Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, vacation rental in Oak Hill

'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
Beautiful Home, Gorgeous View, Spacious Living, vacation rental in Oak Hill

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., vacation rental in Oak Hill

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
Save time - get the best Oak Hill rentals sent straight to your email!
Mountain House Retreat, vacation rental in Oak Hill

Mountain House Retreat

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
FAB FUN GREEN BUILT FARMHOUSE ON 17 ACRES, vacation rental in Oak Hill

FAB FUN GREEN BUILT FARMHOUSE ON 17 ACRES

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Secluded Charming Water Front Log Home, vacation rental in Oak Hill

Secluded Charming Water Front Log Home

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
More info
Check in
Check out
Payment Protection
Cute Condo in The Quads at Windham, vacation rental in Oak Hill

Cute Condo in The Quads at Windham

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Year-Round Relaxing Mountain Escape, vacation rental in Oak Hill

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, vacation rental in Oak Hill

WINDHAM MAGNIFICENT HOLIDAY GETAWAY

5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
More info
Check in
Check out
Payment Protection
Chalet with a Pond and Pool with  Spectacular views of the Catskill Mountains, vacation rental in Oak Hill

Chalet with a Pond and Pool with Spectacular views of the Catskill Mountains

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Mandeville Manor, “Beautiful Fall Foliage”!!!, vacation rental in Oak Hill

Mandeville Manor, “Beautiful Fall Foliage”!!!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Spacious Mountain Escape - Minutes to Windham/Hunter, vacation rental in Oak Hill

Spacious Mountain Escape - Minutes to Windham/Hunter

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Windham Skiers Book Now! Cottage North Catskills, vacation rental in Oak Hill

Windham Skiers Book Now! Cottage North Catskills

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Payment Protection
Historic Catskill Mountain House close to Windham, vacation rental in Oak Hill

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, vacation rental in Oak Hill

Armstrongs Elk Farm

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Windham Mountain Ski House with Great Views, vacation rental in Oak Hill

Windham Mountain Ski House with Great Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Mountain House: The Perfect 4 Season Retreat, vacation rental in Oak Hill

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., vacation rental in Oak Hill

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., vacation rental in Oak Hill

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!, vacation rental in Oak Hill

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, vacation rental in Oak Hill

Meadows, Birdsong, Peace and Quiet

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Xenia, vacation rental in Oak Hill

The Xenia

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
Check in
Check out
Payment Protection
Rare Ski Mountain View!, vacation rental in Oak Hill

Rare Ski Mountain View!

5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Tentrr Signature Site - Creekside Thyme, vacation rental in Oak Hill

Tentrr Signature Site - Creekside Thyme

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Tentrr Signature Site - Creekside Zen in Catskills, vacation rental in Oak Hill

Tentrr Signature Site - Creekside Zen in Catskills

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Catskills Home, 5 Mins to Windham Mtn Resort!, vacation rental in Oak Hill

Catskills Home, 5 Mins to Windham Mtn Resort!

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Country Place Resort Home of Zoom Flume Water park, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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!, vacation rental in Oak Hill

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, vacation rental in Oak Hill

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
Updated Catskills Mtn. Retreat w/ Panoramic Views!, vacation rental in Oak Hill

Updated Catskills Mtn. Retreat w/ Panoramic Views!

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Summer Rental Catskills NY-Minutes to Lakes & Mountains 2.5 hours from NYC, vacation rental in Oak Hill

Summer Rental Catskills NY-Minutes to Lakes & Mountains 2.5 hours from NYC

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Great 5 BR House !!!!, vacation rental in Oak Hill

Great 5 BR House !!!!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Luxury Home w/ Deck: Explore the Catskill Mtns!, vacation rental in Oak Hill

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