Villa Bay - Vacation Rentals in Woodstock

Private countryside apartment suite 1.5 miles to Woodstock From US $132
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
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  • Balcony/Terrace
The Herwood Inn From US $197
         

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9.6 (90 Reviews)
House
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  • TV
Pet Friendly Cabin Doh-Ray up @ 1500 ft From US $311
         

10.0 (67 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace From US $291
         

Luxury Places to Stay in Woodstock

Over 198+ Luxury Places to Stay in or Near Woodstock
Walk To Woodstock, Streamside W/In Ground Pool From US $2,544
         

10.0 (40 Reviews)
House
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  • Pool
The 212 Escape From US $1,725
         

10.0 (1 Review)
House
  • Air Conditioner
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  • Pet Friendly
Luxury Woodstock Family Retreat with pool/hot tub From US $1,069
         

Woodstock Historic Artist Estate - The Museum House From US $871
         

10.0 (6 Reviews)
House
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Woodstock

Over 46+ Top-Rated Vacation Rentals with a Pool in or Near Woodstock
Romantic Luxury Chalet For 2 From US $249
         

10.0 (304 Reviews)
Ski Chalet
  • Air Conditioner
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  • Pet Friendly
HOT TUB w/POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN From US $479
         

10.0 (102 Reviews)
House
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  • Pet Friendly
Mid-Century Modern Gem, Heated Pool, 1 Mile from Town From US $572
         

10.0 (35 Reviews)
House
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  • Pet Friendly
Relax near Catskills in our cozy Woodstock Apartment From US $128
         

10.0 (19 Reviews)
Apartment
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  • Pool
Secluded 3BR Woodland Escape Cottage 4 min from Woodstock From US $630
         

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10.0 (1 Review)
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  • Pet Friendly

Pet-Friendly Vacation Rentals in Woodstock

Over 67+ Pet-Friendly Vacation Rentals in or Near Woodstock
The Herwood Inn From US $363
         

9.4 (71 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly From US $397
         

Cozy and eclectic Woodstock getaway From US $299
         

10.0 (34 Reviews)
Apartment
  • Air Conditioner
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  • Pet Friendly
Private cottage - 5 min from the center of town From US $291
         

10.0 (15 Reviews)
Cottage
  • Air Conditioner
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  • Pet Friendly
Bright, historic Woodstock home close to town From US $465
         

10.0 (13 Reviews)
House
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  • Pet Friendly
  • TV

Large Vacation Homes & Villas in Woodstock

Over 14+ Large Vacation Homes & Villas in or Near Woodstock
Gracious Woodstock Retreat -Walking Distance to Town From US $501
         

Morning Glory B&B Woodstock NY From US $199
         

8.4 (62 Reviews)
Bed & Breakfast
  • Air Conditioner
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  • View
Beautiful & Spacious Woodstock Home w/Pool From US $588
         

8.6 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
The 212 Escape From US $1,033
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
🇺🇦Byrdcliffe Arts Colony in the Catskills w/Hot Tub From US $841
         

Wheelchair Accessible Vacation Homes in Woodstock

Over 5+ Wheelchair Accessible Vacation Homes in or Near Woodstock
Woodstock Way Hotel From US $245
         

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9.2 (184 Reviews)
Hotel
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  • Pet Friendly
Hotel Dylan From US $149
         

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8.9 (121 Reviews)
Hotel
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  • Parking
  • Pet Friendly

Woodstock Varoom and Airbnb Places to Stay Under $200

Over 43+ Woodstock Varoom and Airbnb Places to Stay Under $200
Renovated home seconds from town From US $136
         

10.0 (1 Review)
House
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Twin Gables of Woodstock From US $169
         

9.4 (157 Reviews)
Hotel
  • Air Conditioner
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  • Balcony/Terrace
Hotel Dylan From US $178
         

9.4 (40 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi! From US $195
         

8.2 (10 Reviews)
Apartment
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  • TV

Instantly Bookable Vacation Homes in Woodstock

Over 74+ Instantly Bookable Vacation Homes in or Near Woodstock
Streamside Cottage Half Mile to Town of Woodstock From US $388
         

10.0 (261 Reviews)
Cottage
  • Air Conditioner
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  • TV
Fall Foliage Getaway! From US $473
         

10.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Woodstock Getaway w/Hot Tub ~ 2 Mi to Dtwn! From US $398
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Woodstock Vacation Rentals

With more than 207 Woodstock vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Villa Bay and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Woodstock.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Villa Bay Woodstock, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Woodstock. Places to stay near Woodstock are 838.59 ft² on average, with prices averaging $413 a night.

Villa Bay makes it easy and safe to find and compare vacation rentals in Woodstock with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Woodstock

Type Count
Vacation Homes 118
Holiday Apartments 36
Cottages 27
Cabin Rentals 9
Hotels with Suites 8
Ski Chalet Rentals 3
B&B 2
Others 2
Villas 1

Use these Quick Filters to Find a Vacation Rental in Woodstock

Pro Tip: Villa Bay makes it easy to compare the best listings on Villa Bay homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Villa Bay homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Woodstock.

Weather in Woodstock

View the weather forecast for Woodstock before booking your Woodstock Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Woodstock, NY