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$808 per night from 24 Feb to 25 Feb
AU$808
includes taxes & fees
24 Feb - 25 Feb
Located in Woodstock, this vacation home is on the waterfront, a 2-minute drive from Black Pond and 5 minutes from Campert Preserve.
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
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
When you stay at this vacation home in Holland, you'll be on a lake, within a 5-minute drive of Mashapaug Pond and Bigelow Hollow State Park.
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Beautiful two-story home close to downtown worcester 5beds-4bedroom

Beautiful two-story home close to downtown worcester 5beds-4bedroom

Worcester
The price is AU$619 per night from 24 Feb to 25 Feb
AU$619
includes taxes & fees
24 Feb - 25 Feb
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of DCU Center and Union Station.
Beautiful two-story home close to downtown worcester 5beds-4bedroom
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Quintessential New England Home w/ Patio & Grill!

Quintessential New England Home w/ Patio & Grill!

2 out of 5
Putnam
Located in Putnam, this vacation home is within a 5-minute drive of Bradley Playhouse and Rotary Park.
Quintessential New England Home w/ Patio & Grill!
Spacious family friendly 3BR 1st FL apt. Kelly SQ, collages & universities

Spacious family friendly 3BR 1st FL apt. Kelly SQ, collages & universities

Worcester
With a stay at this vacation home, you'll be centrally located in Worcester, within a 5-minute drive of DCU Center and Union Station.
Spacious family friendly 3BR 1st FL apt. Kelly SQ, collages & universities
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Sturbridge
Located in Sturbridge, this vacation home is on a lake, within a 5-minute drive of Sturbridge Town Hall and Wells State Park.
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Spencer
Located in Spencer, this vacation home is on the waterfront, within a 10-minute drive of Saint Joseph's Abbey and Buck Hill Conservation Dam.
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore
Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds

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

Charlton
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
Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!

Sturbridge
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!
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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
71 Holiday Homes
Lowest Price
AU$184
Highest Price
AU$857
Popular accommodation
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!, Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!, Beautiful two-story home close to downtown worcester 5beds-4bedroom, Quintessential New England Home w/ Patio & Grill!, Spacious family friendly 3BR 1st FL apt. Kelly SQ, collages & universities , Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!, completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore, Holiday Lake House near Treehouse Brewery & Amazon Warehouse with King Beds, Lake House in Sturbridge w/All the Views!

Top trending hotels in Woodstock

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$857 per night from 24 Feb to 25 Feb
AU$857
includes taxes & fees
24 Feb - 25 Feb
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!!
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$808 per night from 24 Feb to 25 Feb
AU$808
includes taxes & fees
24 Feb - 25 Feb
Located in Woodstock, this vacation home is on the waterfront, a 2-minute drive from Black Pond and 5 minutes from Campert Preserve.
Secluded 2-Acre Lakefront Home! Exclusive Off-Season Rates – Book Your Retreat!
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$808 per night from 24 Feb to 25 Feb
AU$808
includes taxes & fees
24 Feb - 25 Feb
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$184 per night from 26 Mar to 27 Mar
AU$184
includes taxes & fees
26 Mar - 27 Mar
A stay at Wellsworth Hotel places you in the heart of Southbridge, steps from Southbridge Town Common and 5 minutes by foot from Windsor Court Historic ...
Wellsworth Hotel
Don't see what you're looking for?
See all available properties in Woodstock
View all properties
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.