Vacation Rentals in Woodstock, NY

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Woodstock, NY

Book a vacation rental in Woodstock that has the highest visitor rating. Here are 6 of the best vacation rentals in Woodstock.
Romantic + historic artist cottage with storybook charm in private woods!
10

Excellent

·
Woodstock
·
2 br
·
Sleeps 4
·
Oven · Fireplace · On Site Laundry ·
From
$266/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Oven
Fireplace
On Site Laundry
Ski In Ski Out
Furnished
Air Conditioning
Fitness Center
Wifi
Other spaces
Balcony, Workspace, Kitchen
Privacy & Luxury @ Heart of Woodstock w/ Hot Tub
10

Excellent

·
Woodstock
·
2 br
·
Sleeps 6
·
Fireplace · Outdoor Space · On Site Laundry ·
From
$308/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Fireplace
On Site Laundry
Hot Tub
Air Conditioning
Dishwasher
Oven
Furnished
Wifi
Other spaces
Kitchen, Balcony, Workspace
Price drop
Woodstock House on 35 private acres Mtn Views
10

Excellent

·
Woodstock
·
3 br
·
Sleeps 6
·
Workspace · Residents Lounge · Kitchen ·
From
$370/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Residents Lounge
On Site Laundry
Furnished
Air Conditioning
Dishwasher
Wifi
Fireplace
Oven
Other spaces
Workspace, Kitchen, Balcony
Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!
10

Excellent

·
Woodstock
·
4 br
·
Sleeps 8
·
Fireplace · Oven · Ceiling Fan ·
From
$331/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Fireplace
Oven
Ceiling Fan
Wifi
On Site Laundry
Furnished
Dishwasher
Air Conditioning
Other spaces
Kitchen
Price drop
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
10

Excellent

·
Woodstock
·
2 br
·
Sleeps 4
·
Air Conditioning · Dishwasher · On Site Laundry ·
From
$303/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Air Conditioning
Dishwasher
On Site Laundry
Oven
Mountains
Carpet
Wifi
Fitness Center
Other spaces
Kitchen, Balcony
Frolic & Focus in this Bright Stylish Woodstock Cottage
10

Excellent

·
Woodstock
·
1 br
·
Sleeps 2
·
Furnished · Outdoor Space · On Site Laundry ·
From
$359/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
On Site Laundry
Air Conditioning
Wifi
Other spaces
Kitchen

Our Recommended Vacation Rentals in Woodstock, NY

We analyzed vacation rentals in Woodstock from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Woodstock to help you find a deal for your next trip.
Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!

No rating

·
Woodstock
·
4 br
·
Sleeps 8
·
Central Heat · Oven · Microwave ·
From
$260/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Central Heat
Oven
Microwave
Air Conditioning
Dishwasher
Ceiling Fan
Fireplace
Free Parking
Other spaces
Kitchen, Garden
Price drop
Charming Cottage with Yard - 2 Mi to Tinker St!
8.9

Very good

·
Woodstock
·
3 br
·
Sleeps 6
·
Kitchen · Wifi · Air Conditioning ·
From
$371/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Wifi
Air Conditioning
Fitness Center
Dishwasher
Free Parking
Furnished
Oven
In Unit Laundry
Other spaces
Kitchen, Workspace
Price drop
Woodstock Getaway with Hot Tub about 2 Mi to Dtwn!

No rating

·
Woodstock
·
4 br
·
Sleeps 8
·
Dishwasher · Outdoor Space · Free Parking ·
From
$414/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Dishwasher
Free Parking
Furnished
Hot Tub
Fireplace
In Unit Laundry
Air Conditioning
Wifi
Other spaces
Kitchen

Budget-Friendly Vacation Rentals in Woodstock, NY

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Woodstock starting at $80. Use the price filter at the top of the page to search for more specific prices.
Cozy and spacious apartment in tree-lined neighborhood

No rating

·
Woodstock
·
2 br
·
Sleeps 6
·
Mountains · Fitness Center · Wifi ·
From
$80/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Mountains
Fitness Center
Wifi
Furnished
In Unit Laundry
Other spaces
Kitchen
Price drop
Charming & Private Guest Cottage
10

Excellent

·
Woodstock
·
1 br
·
Sleeps 3
·
Kitchen · Outdoor Space · Wifi ·
From
$95/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Air Conditioning
Furnished
Oven
Other spaces
Kitchen, Workspace
Price drop
Hotel Woodstock - Queen Anne's Lace Suite
10

Excellent

·
Woodstock
·
1 br
·
Sleeps 3
·
Kitchen · Furnished ·
From
$99/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Other spaces
Kitchen
Hotel Woodstock - Starflower 2D Suite
10

Excellent

·
Woodstock
·
1 br
·
Sleeps 3
·
Kitchen · Furnished · Balcony ·
From
$99/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Other spaces
Kitchen, Balcony
Hotel Woodstock - Iris suite
10

Excellent

·
Woodstock
·
1 br
·
Sleeps 3
·
Air Conditioning · Balcony · Furnished ·
From
$99/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Woodstock Hotel - Aster Suite
10

Excellent

·
Woodstock
·
1 br
·
Sleeps 2
·
Air Conditioning · Kitchen · Balcony ·
From
$99/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Furnished
Other spaces
Kitchen, Balcony

Vacation Rentals With A Pool in Woodstock, NY

Want to relax by the pool? Book one of these Woodstock vacation rentals with a pool.
Price drop
BEAUTIFULLY APPOINTED, Elegant 4+ Br, 10 Pvt Ac, Chef’s Kitchen

No rating

·
Woodstock
·
4 br
·
Sleeps 10
·
Mountains · High Ceilings · Oven ·
From
$850/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Mountains
High Ceilings
Oven
Fitness Center
Air Conditioning
On Site Laundry
Fireplace
Wifi
Other spaces
Kitchen, Workspace
Price drop
Beautiful & Spacious Woodstock Home w/ Pool
10

Excellent

·
Woodstock
·
5 br
·
Sleeps 10
·
Outdoor Space · Kitchen · Wifi ·
From
$340/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Wifi
Swimming Pool
Private Pool
Dishwasher
Fireplace
Pool
On Site Laundry
Air Conditioning
Other spaces
Kitchen
Price drop
Mid-Century Gem with Heated Pool 1 Mile from Town
10

Excellent

·
Woodstock
·
3 br
·
Sleeps 6
·
Kitchen · Outdoor Space · Oven ·
From
$410/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Oven
Air Conditioning
Furnished
Wheelchair Accessible
Dishwasher
On Site Laundry
Fireplace
Private Pool
Other spaces
Kitchen
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Updated: September 27, 2023