Vacation Rentals in Woodstock, NY

PRICE PER NIGHT

ACCOMMODATION TYPES

Spacious, Private, Close to Town, Work From Home
10

Excellent

·
Woodstock
·
3 br
·
Sleeps 7
·
Hot Tub · Workspace · Fireplace ·
From
$302/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Hot Tub
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Workspace, Kitchen
Village Center: Gracious & Spacious Retreat "Above the Books"
9.9

Excellent

·
Woodstock
·
2 br
·
Sleeps 4
·
Assigned Parking · Mountains · Dishwasher ·
From
$163/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Assigned Parking
Mountains
Dishwasher
Air Conditioning
In Unit Laundry
Wifi
Furnished
Roof Deck
Other spaces
Kitchen
Romantic Luxury Chalet with Private Pool
9.8

Excellent

·
Woodstock
·
Studio
·
Sleeps 2
·
Pool · Private Pool · Balcony ·
From
$308/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
Pool
Private Pool
Ski In Ski Out
Fireplace
Air Conditioning
In Unit Laundry
Oven
Wifi
Other spaces
Balcony, Kitchen
Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!
9.9

Excellent

·
Woodstock
·
3 br
·
Sleeps 6
·
Balcony · Ski In Ski Out · Fitness Center ·
From
$345/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Ski In Ski Out
Fitness Center
Mountains
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Other spaces
Balcony, Kitchen
TOP RATED! Romantic rustic luxury+flowing stream+walk to town=Brook Cottage
9.9

Excellent

·
Woodstock
·
2 br
·
Sleeps 4
·
Carpet · Ceiling Fan · Balcony ·
From
$341/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Carpet
Ceiling Fan
Fitness Center
Mountains
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Other spaces
Balcony, Kitchen
Gracious Woodstock Retreat -Walking Distance to Town
10

Excellent

·
Woodstock
·
4 br
·
Sleeps 10
·
Ev Charging · Lake · Waterfront ·
From
$295/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Ev Charging
Lake
Waterfront
Ski In Ski Out
Fitness Center
Mountains
Fireplace
Dishwasher
Other spaces
Kitchen
Cosy Catskills Cabin, minutes to Woodstock Village.

No reviews

·
Woodstock
·
2 br
·
Fitness Center · Outdoor Space · Air Conditioning ·
From
$208/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Fitness Center
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Kitchen
Fabulous Newly Renovated Family House Near Woodstock Center
10

Excellent

·
Woodstock
·
4 br
·
Sleeps 8
·
Fireplace · Dishwasher · Outdoor Space ·
From
$425/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Kitchen

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Woodstock Country Guest Suite
9.7

Excellent

·
Woodstock
·
1 br
·
Sleeps 2
·
Fitness Center · Outdoor Space · Air Conditioning ·
From
$135/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Kitchen
New Luxury 5BR Woodstock Secret Retreat Near all Ski MT Heated Pool& Hot Tub
9.4

Excellent

·
Woodstock
·
5 br
·
Sleeps 13
·
Hot Tub · Pool · Private Pool ·
From
$1,153/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Hot Tub
Pool
Private Pool
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Other spaces
Balcony, Workspace, Kitchen
Mountainside home, with pool , deck & 3mins to Woodstock

No reviews

·
Woodstock
·
4 br
·
Sleeps 6
·
Balcony · Workspace · Mountains ·
From
$542/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Mountains
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Balcony, Workspace, Kitchen
Charming & Private Guest Cottage
9.5

Excellent

·
Woodstock
·
1 br
·
Sleeps 3
·
Workspace · Outdoor Space · Air Conditioning ·
From
$178/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Oven
Wifi
Furnished
Other spaces
Workspace, Kitchen
COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!
9.7

Excellent

·
Woodstock
·
3 br
·
Sleeps 6
·
Pool · Private Pool · Fitness Center ·
From
$430/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Pool
Private Pool
Fitness Center
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Other spaces
Kitchen
SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN
10

Excellent

·
Woodstock
·
3 br
·
Sleeps 8
·
High Ceilings · Hot Tub · Waterfront ·
From
$562/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
High Ceilings
Hot Tub
Waterfront
Pool
Private Pool
Fitness Center
Fireplace
Dishwasher
Other spaces
Kitchen
Magical Chalet with spectacular views
9.7

Excellent

·
Woodstock
·
4 br
·
Sleeps 8
·
Deck · Ev Charging · Lake ·
From
$824/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Ev Charging
Lake
Waterfront
Pool
Private Pool
Ski In Ski Out
Fitness Center
Mountains
Other spaces
Deck, Balcony, Workspace, Kitchen
Woodstock Mid-Century Gem in the Woods - Secluded Getaway Close to Town
10

Excellent

·
Woodstock
·
3 br
·
Sleeps 5
·
On Site Laundry · Workspace · Fireplace ·
From
$358/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
On Site Laundry
Fireplace
Dishwasher
In Unit Laundry
Oven
Wifi
Furnished
Fitness Center
Other spaces
Workspace, Kitchen
Charming Getaway in Woodstock

No reviews

·
Woodstock
·
5 br
·
Sleeps 10
·
Lake · Hot Tub · Waterfront ·
From
$500/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Lake
Hot Tub
Waterfront
Ski In Ski Out
Mountains
Fireplace
Dishwasher
Air Conditioning
Other spaces
Workspace, Kitchen
INCREDIBLE “WALKABLE” RENTAL with Sawkill Creek Views
10

Excellent

·
Woodstock
·
2 br
·
Sleeps 4
·
Hardwood Floor · Ski In Ski Out · Fireplace ·
From
$411/night
Check availability
Property
Apartment · 2 Beds · 3 baths
Amenities
Hardwood Floor
Ski In Ski Out
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
Streamside Cottage Walking Distance to Town of Woodstock
9.9

Excellent

·
Woodstock
·
1 br
·
Sleeps 4
·
Waterfront · Workspace · Fitness Center ·
From
$193/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Waterfront
Fitness Center
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Workspace, Kitchen
'Casa Reál' ~ Expansive Woodstock House w/ Hot Tub
9.8

Excellent

·
Woodstock
·
4 br
·
Sleeps 8
·
Hardwood Floor · Hot Tub · Ski In Ski Out ·
From
$225/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Hardwood Floor
Hot Tub
Ski In Ski Out
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Other spaces
Kitchen
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10

Excellent

·
Woodstock
·
2 br
·
Sleeps 4
·
High Ceilings · Mountains · Fireplace ·
From
$290/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
High Ceilings
Mountains
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
EASY WALK TO TOWN Office, Fireplace, Game Room w. Pool Table HOT TUB!
10

Excellent

·
Woodstock
·
5 br
·
On Site Laundry · Ceiling Fan · Hot Tub ·
From
$303/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
On Site Laundry
Ceiling Fan
Hot Tub
Waterfront
Ski In Ski Out
Fitness Center
Fireplace
Dishwasher
Other spaces
Workspace, Kitchen
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
9.6

Excellent

·
Woodstock
·
1 br
·
Sleeps 2
·
Ski In Ski Out · Workspace · Fitness Center ·
From
$199/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Ski In Ski Out
Fitness Center
Mountains
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Workspace, Kitchen
Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.
10

Excellent

·
Woodstock
·
3 br
·
Ski In Ski Out · Workspace · Fitness Center ·
From
$317/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Ski In Ski Out
Fitness Center
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Other spaces
Workspace, Kitchen
IMAGINE WOODSTOCK FIELD STUDIO
7.3

Very good

·
Woodstock
·
1 br
·
Sleeps 3
·
Ski In Ski Out · Fitness Center · Air Conditioning ·
From
$143/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Ski In Ski Out
Fitness Center
Air Conditioning
Oven
Wifi
Furnished
Other spaces
Kitchen
Woodstock Paradise with Gardens & Private Heated Pool (seasonal)
10

Excellent

·
Woodstock
·
2 br
·
Sleeps 4
·
Carpet · Hardwood Floor · Pool ·
From
$388/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Carpet
Hardwood Floor
Pool
Private Pool
Ski In Ski Out
Fitness Center
Mountains
Fireplace
Other spaces
Kitchen
Room 6- Twin Gables of Woodstock
8

Very good

·
Woodstock
·
1 br
·
Sleeps 1
·
Ski In Ski Out · Workspace · Mountains ·
From
$122/night
Check availability
Property
House · 1 Bed · 3 baths
Amenities
Ski In Ski Out
Mountains
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Workspace
Room 7- Twin Gables of Woodstock
10

Excellent

·
Woodstock
·
1 br
·
Sleeps 1
·
Ski In Ski Out · Workspace · Mountains ·
From
$123/night
Check availability
Property
House · 1 Bed · 3 baths
Amenities
Ski In Ski Out
Mountains
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Workspace
JUST LISTED! Romance +history +luxury +privacy in heart of village = Maple House
10

Excellent

·
Woodstock
·
2 br
·
Sleeps 4
·
High Ceilings · Hardwood Floor · Ceiling Fan ·
From
$330/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
High Ceilings
Hardwood Floor
Ceiling Fan
Fitness Center
Mountains
Fireplace
Dishwasher
Air Conditioning
Other spaces
Kitchen
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
9.9

Excellent

·
Woodstock
·
1 br
·
Sleeps 2
·
Carpet · Hardwood Floor · Waterfront ·
From
$271/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Carpet
Hardwood Floor
Waterfront
Ski In Ski Out
Fitness Center
Mountains
Fireplace
Dishwasher
Other spaces
Kitchen
Serene Woodstock 3 bedroom cottage with sweeping mountain views
10

Excellent

·
Woodstock
·
3 br
·
Sleeps 5
·
Workspace · Mountains · Dishwasher ·
From
$296/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Mountains
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Onsite Management
Other spaces
Workspace, Kitchen
'Casa Reál' ~ Expansive Woodstock House w/ Hot Tub
9.6

Excellent

·
Woodstock
·
4 br
·
Sleeps 8
·
Toiletries · Garden · Tv ·
From
$150/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Toiletries
Tv
Microwave
Assigned Parking
Central Heat
Free Parking
Ceiling Fan
Fireplace
Other spaces
Garden, Kitchen
NEW! Charming Cottage w/ Yard - 2 Mi to Tinker St!
9.4

Excellent

·
Woodstock
·
3 br
·
Sleeps 6
·
Walk In Closets · Toiletries · Garden ·
From
$295/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Walk In Closets
Toiletries
Tv
Microwave
Central Heat
Free Parking
Ceiling Fan
Fitness Center
Other spaces
Garden, Kitchen
Gorgeous Villa w/ Mountain Views, pool, hot tub!
9.4

Excellent

·
Woodstock
·
3 br
·
Sleeps 8
·
Hot Tub · Pool · Private Pool ·
From
$488/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Hot Tub
Pool
Private Pool
Mountains
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
MONTH! History+art+luxury+style=Byrdcliffe Retreat w/separate office+heated pool
10

Excellent

·
Woodstock
·
3 br
·
Sleeps 6
·
On Site Laundry · Central Heat · High Ceilings ·
From
$778/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
On Site Laundry
Central Heat
High Ceilings
Pool
Private Pool
Fitness Center
Mountains
Dishwasher
Other spaces
Workspace, Kitchen
Wydeclove Artist Retreat
10

Excellent

·
Woodstock
·
1 br
·
Sleeps 2
·
Fitness Center · Mountains · Outdoor Space ·
From
$213/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Fitness Center
Mountains
Air Conditioning
In Unit Laundry
Wifi
Furnished
Other spaces
Kitchen
NEW! Rock City Writer's Studio: Bucolic Setting, Nordic Sauna, Walk to Town!
9.7

Excellent

·
Woodstock
·
Studio
·
Sleeps 2
·
Assigned Parking · Ski In Ski Out · Fitness Center ·
From
$126/night
Check availability
Property
Apartment · Studio · 2 baths
Amenities
Assigned Parking
Ski In Ski Out
Fitness Center
Mountains
In Unit Laundry
Wifi
Furnished
Other spaces
Kitchen
Hotel Woodstock - Starflower 2D Suite
9.6

Excellent

·
Woodstock
·
1 br
·
Sleeps 3
·
Balcony · Kitchen · Furnished ·
From
$99/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Other spaces
Balcony, Kitchen
Hotel Woodstock - Iris suite
9.6

Excellent

·
Woodstock
·
1 br
·
Sleeps 3
·
Balcony · Air Conditioning · Kitchen ·
From
$99/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Celebrate Woodstock & the Surrounding Area, Walk To Town, Swimming Pond.
10

Excellent

·
Woodstock
·
2 br
·
Sleeps 4
·
Beach · Waterfront · Pool ·
From
$250/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Beach
Waterfront
Pool
Private Pool
Ski In Ski Out
Fitness Center
Mountains
Air Conditioning
Other spaces
Balcony, Kitchen
Charming Cottage with Yard - 2 Mi to Tinker St!
9.2

Excellent

·
Woodstock
·
3 br
·
Sleeps 6
·
Free Parking · Dishwasher · Outdoor Space ·
From
$360/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Free Parking
Dishwasher
In Unit Laundry
Oven
Wifi
Furnished
Fitness Center
Other spaces
Kitchen
Woodstock Getaway with Hot Tub about 2 Mi to Dtwn!

No reviews

·
Woodstock
·
4 br
·
Sleeps 8
·
Free Parking · Hot Tub · Fireplace ·
From
$306/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Free Parking
Hot Tub
Fireplace
Dishwasher
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Kitchen
Cozy Woodstock Home with Fire Pit!

No reviews

·
Woodstock
·
1 br
·
Sleeps 4
·
Free Parking · Dishwasher · Outdoor Space ·
From
$230/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Free Parking
Dishwasher
Oven
Wifi
Furnished
Other spaces
Kitchen
Private apartment suite, dedicated WiFi, easy access to Woodstock village
10

Excellent

·
Woodstock
·
1 br
·
Sleeps 2
·
Pool · Private Pool · Balcony ·
From
$91/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Pool
Private Pool
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Balcony, Workspace, Kitchen
Newly built Modern Cabin walk to town

No reviews

·
Woodstock
·
1 br
·
Sleeps 2
·
Air Conditioning · Wifi · Furnished ·
From
$250/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Air Conditioning
Wifi
Furnished
Modern Glass House, Minutes to Town
10

Excellent

·
Woodstock
·
3 br
·
Sleeps 8
·
Hot Tub · Waterfront · Pool ·
From
$1,250/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Hot Tub
Waterfront
Pool
Private Pool
Mountains
Fireplace
Dishwasher
Air Conditioning
Other spaces
Balcony, Workspace, Kitchen
Romantic Mountaintop Studio🏡 Country Vibe Ski⛷️ Hike Dine Charming Private🥂
9.8

Excellent

·
Woodstock
·
1 br
·
Sleeps 3
·
Ceiling Fan · Waterfront · Pool ·
From
$225/night
Check availability
Property
Apartment · 1 Bed · 2 baths
Amenities
Ceiling Fan
Waterfront
Pool
Private Pool
Ski In Ski Out
Fitness Center
Mountains
Dishwasher
Other spaces
Balcony, Kitchen
Moutain home in world famous Woodstock, NY, great views, 2 hours from NYC
10

Excellent

·
Woodstock
·
3 br
·
Sleeps 4
·
Balcony · Workspace · Fitness Center ·
From
$223/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Fitness Center
Mountains
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Wifi
Furnished
Other spaces
Balcony, Workspace, Kitchen
Extraordinary modern renovated 1840's barn with pool and privacy
9.9

Excellent

·
Woodstock
·
4 br
·
Sleeps 6
·
High Ceilings · Pool · Private Pool ·
From
$622/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
High Ceilings
Pool
Private Pool
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Oven
Other spaces
Balcony, Workspace, Kitchen
Woodstock Hotel - Aster Suite
9.4

Excellent

·
Woodstock
·
1 br
·
Sleeps 2
·
Balcony · Air Conditioning · Kitchen ·
From
$99/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Showing 1 - 50 of 133 results
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Home > New-york Vacation Rentals > Woodstock Vacation Rentals
Updated: March 24, 2023

Learn about vacation rentals in

Woodstock

Explore 135 vacation rentals near Woodstock, New York. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Woodstock, you can see photos of Woodstock vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Woodstock vacation rentals in specific areas. Whether you’re looking for a Woodstock staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Woodstock is $91 per night and the highest price is $1,250 per night.
19 of the vacation rentals near Woodstock are apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation units is $112 per night. There are currently 10 vacation units under this price. 81 of the vacation rentals near Woodstock are houses. The average bathroom count for a vacation house near Woodstock is 2. The average price for vacation houses near Woodstock is $392 per night. There are 51 vacation homes under this price. The most common amenities for vacation rentals near Woodstock are: furnished, kitchen, and wifi. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

1 bed rentals

45 available

2 bed rentals

29 available

3 bed rentals

32 available

4+ bed rentals

23 available

Getting around Woodstock

Walking

3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).

Car

10/10
Commuting is easy with multiple accessible routes and plenty of parking.

Points of interest in Woodstock

Groceries

3/10
At least one grocery store within a 30-minute walk

Shopping

3/10
Some shops within walking distance

Cafes

2/10
Few or no cafés within walking distance

Restaurants

4/10
Some restaurants within walking distance

Nightlife

1/10
Few or no bars within walking distance

Vacation Rentals in Woodstock, NY FAQ

How many vacation rentals in Woodstock are available?

There are currently 135 vacation rentals in Woodstock available. Our vacation rentals in Woodstock include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Woodstock?

Yes, right now there are 43 pet friendly vacation rentals in Woodstock. A pet friendly vacation rental in Woodstock means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Woodstock with a pool?

Yes there are vacation rentals with a pool available in Woodstock, NY. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Woodstock with internet access?

As of March 24, 2023, there are vacation rentals with internet access available in Woodstock, New York. Check out more enjoyable destinations on Vacations by Zumper.

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