Discover Your Perfect Woodstock Vacation Homes

Woodstock Pet Friendly Vacation Rentals

9.5 (56 Reviews)
Hotel
The Herwood Inn
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
|
8.9 (91 Reviews)
Hotel
Hotel Dylan
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in Woodstock on PetFriendly.io

Woodstock Large Vacation Homes

See More Family Vacation Rentals in Woodstock on FVR

Why Choose Rent By Owner for your Woodstock Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Woodstock Vacation Rentals

Where are the best neighborhoods to stay in Woodstock?

When planning your stay in Woodstock, New York, exploring the diverse neighborhoods can enhance your overall experience. Whether you prefer a vibrant area close to local shops and art galleries or a tranquil setting surrounded by nature, each neighborhood offers unique charm and convenience. Choosing the right location will ensure you enjoy the authentic atmosphere of Woodstock while having easy access to the area's natural beauty and cultural attractions. With dependable vacation rentals available throughout the town, you'll find the perfect home base for your memorable retreat in this renowned arts community.

Shady

Nestled within the scenic surroundings of Woodstock, Shady offers an inviting retreat where you can enjoy the tranquility and natural beauty of the region. Here, your stay provides easy access to the area's charming atmosphere while maintaining a peaceful ambiance.

View 144+ Rentals in Shady

Best Times to Visit Woodstock

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this destination ensures you can experience its natural beauty and vibrant local culture, making your stay in Woodstock's vacation rentals truly memorable.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, the area comes alive with blooming flowers and vibrant landscapes, making it an ideal time for enjoying the natural beauty of this destination.

Average Temperature Daytime: about 55°F to 70°F - Nighttime: around 35°F to 45°F
autumn
Fall (September to November)

Autumn offers a spectacular display of colorful foliage, attracting visitors seeking picturesque scenery and outdoor activities in the region.

Average Temperature Daytime: roughly 60°F to 70°F - Nighttime: approximately 40°F to 50°F

Off-Season Highlights

image
Summer (June to August)

While summer is popular for outdoor pursuits, early and late summer can be quieter, providing a more relaxed experience for those visiting here.

Average Temperature Daytime: around 75°F to 85°F - Nighttime: about 55°F to 65°F
image
Winter (December to February)

During winter, the region transforms into a peaceful retreat, perfect for travelers seeking solitude and cozy getaways amidst snowy scenery.

Average Temperature Daytime: roughly 25°F to 35°F - Nighttime: close to 15°F to 25°F

Weekly Weather Forecast for Woodstock

How to Book Your Woodstock Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Woodstock

More Top-Rated Vacation Rentals in Woodstock Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor space with a spacious lawn for picnics and relaxation amid the scenic surroundings.
  • Benefit from access to a barbecue grill, perfect for outdoor cooking during your stay in this region.
  • Take advantage of a fire pit, ideal for cozy evenings and gathering with friends or family under the stars.
  • Experience the convenience of outdoor furniture like patio tables and loungers to unwind comfortably outside.
  • Explore well-maintained walking trails or nature paths that start right at your rental’s doorstep.
  • Utilize outdoor recreational amenities such as a swimming pool or hot tub, if available, for added relaxation.
  • Make use of a dedicated outdoor dining area to enjoy meals surrounded by the natural beauty here in the area.

Top Attractions Around Woodstock

What attractions are nearby?

During your stay, you'll have the opportunity to explore nearby hiking trails, art galleries, and local shops that showcase the vibrant culture of this charming region.

image
image

Family Activities

  • Woodstock Farm Sanctuary: Visit this inspiring sanctuary to engage with rescued farm animals, offering an educational and heartwarming experience for the whole family.
  • Woodstock Music Shop: Explore this historic shop that celebrates the area's musical heritage, providing a fun and interactive way for kids and parents to connect over local culture.
  • Overlook Mountain Trail: Embark on a family-friendly hike up to scenic vistas and the remains of an old hotel, perfect for outdoor adventures in the region's natural beauty.
  • Woodstock Playhouse: Enjoy a live performance or a family-friendly show at this renowned local theater, enriching your visit with cultural entertainment unique to here.
image

Adult Activities

  • Exploring local art galleries: Discover a vibrant collection of contemporary and traditional artwork that showcases the region’s rich creative spirit, perfect for art enthusiasts staying nearby.
  • Enjoying live music venues: Experience the area's thriving music scene by visiting intimate venues where talented artists perform, offering an authentic cultural experience during your stay.
  • Participating in outdoor adventures: Engage in scenic hikes or leisurely nature walks through lush landscapes, allowing you to embrace the natural beauty that surrounds this destination.
  • Visiting charming cafes and eateries: Savor locally sourced cuisine and cozy atmospheres at popular spots frequented by locals, making your stay here truly memorable.

Other Places to Stay in Woodstock, NY

Woodstock Public Library
Woodstock Public Library Vacation Rentals
Woodstock Music Shop
Woodstock Music Shop Vacation Rentals
Woodstock Golf Club
Woodstock Golf Club Vacation Rentals
SweetHeart Gallery
SweetHeart Gallery Vacation Rentals
Zena
Zena Vacation Rentals
Thorn Preserve - Catskill Center
Thorn Preserve - Catskill Center Vacation Rentals
Overlook Mountain Trailhead
Overlook Mountain Trailhead Vacation Rentals
Karma Triyana Dharmachakra Monastery
Karma Triyana Dharmachakra Monastery Vacation Rentals
Shady
Shady Vacation Rentals
More Places to Stay Near Woodstock

Woodstock Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local art and music scenes: Immerse yourself in the vibrant cultural atmosphere that makes this destination unique by visiting galleries and live performances around town.
  • Plan outdoor adventures during the right season: Take advantage of the region’s natural beauty by scheduling hikes, outdoor activities, or scenic drives when the weather is most favorable.
  • Sample regional cuisine at nearby eateries: Discover the flavors that define this area by trying local restaurants and cafes offering authentic regional dishes.
  • Choose a well-located vacation rental: Select accommodations near popular attractions and amenities to maximize your time exploring and relaxing here.

Transportation Options

  • Car Rentals: You can explore the region conveniently by renting a car, giving you the freedom to visit surrounding attractions at your own pace.
  • Public Transportation: The area's local bus services offer affordable and accessible options for getting around Woodstock and nearby towns.
  • Taxi and Ride-Sharing Services: Reliable taxi and ride-sharing providers are available for comfortable, on-demand transportation within this destination.
  • Bicycle Rentals: For a scenic and eco-friendly way to experience the area, bicycle rentals provide an excellent option for exploring outdoor trails and charming streets.

Local Customs Options

  • Respect for Artistic Expression: Embrace the region’s rich artistic heritage by participating in local art events and supporting creative communities here.
  • Farmers’ Market Traditions: Visiting the area’s farmers' markets allows you to connect with local vendors and experience authentic regional flavors.
  • Music and Festival Etiquette: Attend concerts and festivals with an appreciation for the area's vibrant music scene and laid-back, friendly atmosphere.
  • Environmental Awareness: Engage in eco-friendly practices as sustainability is highly valued in this destination’s natural and cultural landscape.

Frequently Asked Questions About Woodstock?

1. What are the top vacation rentals in Woodstock?

There are a lot of options in Woodstock. If you plan on staying in the Woodstock area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Woodstock:

2. How many vacation rentals have private pools in Woodstock?

There are 14 vacation rentals with private pools near Woodstock. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Woodstock are best for families?

If you are looking for a family-friendly vacation home in Woodstock, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Woodstock:

4. How many Rentbyowner vacation rentals are available in Woodstock?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 201 in the Woodstock area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Woodstock. 

5. What is the cancellation policy for vacation rentals in Woodstock, New York?

The cancellation policies vary depending on the specific listing. You should review the cancellation terms on the property’s page or contact the owner directly to understand the refund options and any applicable fees.

6. Are there any special requirements or house rules I should be aware of when booking a rental here?

Each vacation rental in the area may have its own set of rules, such as check-in/check-out times, pet policies, or noise restrictions. Always read the house rules listed with the property or communicate directly with the owner to ensure a smooth stay.

7. How do I find the best vacation rental deals in this destination?

To secure the best offers, filter your search by price, amenities, and guest reviews on the listing platform. Early bookings and flexible dates can also help you access significant discounts on vacation rentals in the region.

8. What amenities are typically included in Woodstock vacation rentals?

Most vacation rentals in this area offer amenities like Wi-Fi, fully equipped kitchens, free parking, and outdoor spaces. However, it’s best to check each listing for specific features to match your needs.

9. How do I contact the property owner if I have questions about my booking?

You can typically reach the owner through the messaging system on the booking platform. For detailed inquiries, use the contact details provided in the listing to ensure your questions are addressed before confirming your reservation.

Woodstock Top Rated Vacation Rentals

See More Woodstock Vacation Rentals