Book Holiday Homes in Woodstock

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Featured Holiday Homes in Woodstock

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Woodstock
The price is NZ$902 per night from 4 Jan to 5 Jan
NZ$902
includes taxes & fees
4 Jan - 5 Jan 2025
Stay at this vacation home in Woodstock. Enjoy free WiFi, a garden, and patios. Popular attractions Bishop Preserve and Taylor Brooke Winery are located ...
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
The Tree House at Underhill Hollow

The Tree House at Underhill Hollow

Thompson
Stay at this vacation home in Windham County. Enjoy free WiFi, a garden, and patios. Popular attractions Thompson International Speedway and Quaddick Reservoir ...
The Tree House at Underhill Hollow
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

Woodstock
The price is NZ$902 per night from 4 Jan to 5 Jan
NZ$902
includes taxes & fees
4 Jan - 5 Jan 2025
Book a stay at this beach vacation home in Woodstock. Enjoy free WiFi, a beach locale, and patios. Popular attractions Roseland Cottage and Taylor Brooke Winery ...
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!
Save an average of 15% on thousands of hotels when you're signed in
Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!

Sturbridge
The price is NZ$1,693 per night from 24 Dec to 25 Dec
NZ$1,693
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in Sturbridge. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Old Sturbridge Village and Village Common ...
Lake House in Sturbridge w/All the Views!
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Holland
Stay at this vacation home in Holland. Enjoy free WiFi, a garden, and patios. Our guests praise the property condition in our reviews. Popular attractions Old ...
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds

Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds

Charlton
The price is NZ$1,352 per night from 1 Jan to 2 Jan
NZ$1,352
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this vacation home in Charlton. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Capen Hill Nature Sanctuary and Charlton ...
Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds
Cozy 2-Floor Apartment with Garage Access

Cozy 2-Floor Apartment with Garage Access

Worcester
Stay at this vacation home in Worcester. Enjoy free WiFi, a garden, and patios. Popular attractions Fitton Football Stadium and The Hanover Theatre for the Performing ...
Cozy 2-Floor Apartment with Garage Access
5 bedrooms Home away from Home

5 bedrooms Home away from Home

Leicester
Book a stay at this business-friendly vacation home in Leicester. Enjoy free WiFi, a fitness center, and patios. Popular attractions Charlton Town Common and ...
5 bedrooms Home away from Home
Full family home 200 ft from the lake shore. Dog friendly!

Full family home 200 ft from the lake shore. Dog friendly!

West Brookfield
The price is NZ$1,023 per night from 6 Jan to 7 Jan
NZ$1,023
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this vacation home in West Brookfield. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Rock House Reservation and Quaboag ...
Full family home 200 ft from the lake shore. Dog friendly!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Woodstock Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Woodstock vacation homes are the perfect way for you to wing it.

Holiday houses in Woodstock let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Woodstock in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Woodstock adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Woodstock with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Woodstock vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Woodstock Holiday Homes essential information

Accommodation
72 Holiday Homes
Lowest Price
NZ$190
Highest Price
NZ$1,693
Popular accommodation
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!, The Tree House at Underhill Hollow, Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!, Lake House in Sturbridge w/All the Views!, Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!, Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds, Cozy 2-Floor Apartment with Garage Access, 5 bedrooms Home away from Home , Full family home 200 ft from the lake shore. Dog friendly!

Top trending hotels in Woodstock

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!

Woodstock
The price is NZ$902 per night from 4 Jan to 5 Jan
NZ$902
includes taxes & fees
4 Jan - 5 Jan 2025
Stay at this vacation home in Woodstock. Enjoy free WiFi, a garden, and patios. Popular attractions Bishop Preserve and Taylor Brooke Winery are located ...
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
Famous Waterfront Inn with Jacuzzis, Stunning amenities and unmatched comforts!!

Famous Waterfront Inn with Jacuzzis, Stunning amenities and unmatched comforts!!

Woodstock
The price is NZ$958 per night from 24 Dec to 25 Dec
NZ$958
includes taxes & fees
24 Dec - 25 Dec
Book a stay at this golf castle in Woodstock. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Woodstock Golf Course and Roseland Cottage ...
Famous Waterfront Inn with Jacuzzis, Stunning amenities and unmatched comforts!!
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

Woodstock
The price is NZ$902 per night from 4 Jan to 5 Jan
NZ$902
includes taxes & fees
4 Jan - 5 Jan 2025
Book a stay at this beach vacation home in Woodstock. Enjoy free WiFi, a beach locale, and patios. Popular attractions Roseland Cottage and Taylor Brooke Winery ...
Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!
Save an average of 15% on thousands of hotels when you're signed in
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is NZ$190 per night from 25 Dec to 26 Dec
NZ$190
includes taxes & fees
25 Dec - 26 Dec
Stay at this 3-star business-friendly hotel in Southbridge. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Wellsworth Hotel
Don't see what you're looking for?
See all available properties in Woodstock
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.