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 AU$822 per night from 2 Jan to 3 Jan
AU$822
includes taxes & fees
2 Jan - 3 Jan 2025
Located in Woodstock, this vacation home is on the waterfront, within a 10-minute drive of Bigelow Hollow State Park and Bishop Preserve.
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
The price is AU$302 per night from 27 Dec to 28 Dec
AU$302
includes taxes & fees
27 Dec - 28 Dec
This vacation home is 3.5 mi (5.6 km) from Thompson International Speedway and 4.8 mi (7.8 km) from Bradley Playhouse.
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 AU$822 per night from 2 Jan to 3 Jan
AU$822
includes taxes & fees
2 Jan - 3 Jan 2025
When you stay at this vacation home in Woodstock, you'll be on the beach, within a 5-minute drive of Taylor Brooke Winery and Roseland Cottage.
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 AU$1,538 per night from 23 Dec to 24 Dec
AU$1,538
includes taxes & fees
23 Dec - 24 Dec
When you stay at this vacation home in Sturbridge, you'll be on the waterfront, within a 5-minute drive of Old Sturbridge Village and St. Anne's Shrine.
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
With a stay at this vacation home in Holland, you'll be on a lake, within a 15-minute drive of Old Sturbridge Village and Mashapaug Pond.
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 AU$1,237 per night from 1 Jan to 2 Jan
AU$1,237
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Charlton, this vacation home is within a 10-minute drive of Capen Hill Nature Sanctuary and Charlton Town Common.
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
Located in Worcester (Main South), this vacation home is within a 15-minute walk of Clark University and Burnside Fountain.
Cozy 2-Floor Apartment with Garage Access
5 bedrooms Home away from Home

5 bedrooms Home away from Home

Leicester
When you stay at this vacation home in Leicester, you'll be 8 minutes by car from Vibra Hospital of Western Massachusetts - Central Campus.
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 AU$935 per night from 6 Jan to 7 Jan
AU$935
includes taxes & fees
6 Jan - 7 Jan 2025
Located in West Brookfield, this vacation home is a 2-minute drive from Quaboag River and 6 minutes from Rock House Reservation.
Full family home 200 ft from the lake shore. Dog friendly!
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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.

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
AU$168
Highest Price
AU$1,538
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 AU$822 per night from 2 Jan to 3 Jan
AU$822
includes taxes & fees
2 Jan - 3 Jan 2025
Located in Woodstock, this vacation home is on the waterfront, within a 10-minute drive of Bigelow Hollow State Park and Bishop Preserve.
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 AU$875 per night from 23 Dec to 24 Dec
AU$875
includes taxes & fees
23 Dec - 24 Dec
A stay at this castle places you in the heart of Woodstock, within a 5-minute drive of Roseland Cottage and Woodstock Golf Course.
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 AU$822 per night from 2 Jan to 3 Jan
AU$822
includes taxes & fees
2 Jan - 3 Jan 2025
When you stay at this vacation home in Woodstock, you'll be on the beach, within a 5-minute drive of Taylor Brooke Winery and Roseland Cottage.
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 AU$168 per night from 24 Dec to 25 Dec
AU$168
includes taxes & fees
24 Dec - 25 Dec
With a stay at Wellsworth Hotel, you'll be centrally located in Southbridge, within a 10-minute drive of Old Sturbridge Village and Southbridge Town Common.
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.