Book Holiday Homes in Woodstock

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Featured Holiday Homes in Woodstock

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

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

Worcester
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
SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC

West Brookfield
With a stay at this vacation home in West Brookfield, you'll be within a 15-minute drive of Quaboag River and Rock House Reservation.
SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC
The Bungalow at Eagleville Lake 
Under 3 miles to UCONN!

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

Coventry
With a stay at this vacation home in Coventry, you'll be on the waterfront, within a 5-minute drive of University of Connecticut and J. M. Sarnik & Sons' The ...
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
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Spacious Oxford Home w/ Pool - 4 Mi to Lake!

Spacious Oxford Home w/ Pool - 4 Mi to Lake!

Oxford
With a stay at this vacation home in Oxford, you'll be within a 10-minute drive of Lake Chaubunagungamaug and Sutton Pond.
Spacious Oxford Home w/ Pool - 4 Mi to Lake!
Amazing lake house with everything you need!

Amazing lake house with everything you need!

Ashford
Located in Ashford, this vacation home is on a lake, within a 10-minute drive of Tinkerville Brook Reserve and Iron Mine Valley Preserve.
Amazing lake house with everything you need!
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Ashford
The price is AU$449 per night from 30 Apr to 1 May
AU$449
includes taxes & fees
30 Apr - 1 May
Located in Ashford, this vacation home is on the waterfront, within a 10-minute drive of Tinkerville Brook Reserve and Iron Mine Valley Preserve.
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Home in the woods

Home in the woods

Monson
Located in Monson, this vacation home is in a rural location, within a 10-minute drive of Crane Hill Disc Golf Course and Quaboag River.
Home in the woods
Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!

Sturbridge
The price is AU$1,129 per night from 29 Apr to 30 Apr
AU$1,129
includes taxes & fees
29 Apr - 30 Apr
With a 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!
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$956 per night from 29 Apr to 30 Apr
AU$956
includes taxes & fees
29 Apr - 30 Apr
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!
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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
90 Holiday Homes
Lowest Price
AU$187
Highest Price
AU$1,253
Popular accommodation
Beautiful two-story home close to downtown worcester 5beds-4bedroom, SunnyBrook House - 5 bedroom house in wonderful West Brookfield with WiFi, AC, The Bungalow at Eagleville Lake Under 3 miles to UCONN! , Spacious Oxford Home w/ Pool - 4 Mi to Lake!, Amazing lake house with everything you need! , Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD, Home in the woods, Lake House in Sturbridge w/All the Views!, Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!

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$1,253 per night from 27 May to 28 May
AU$1,253
includes taxes & fees
27 May - 28 May
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$956 per night from 29 Apr to 30 Apr
AU$956
includes taxes & fees
29 Apr - 30 Apr
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!
Inn on Storrs

Inn on Storrs

3.5 out of 5
123 Storrs Road, Willimantic, CT
Fully refundableReserve now, pay when you stay
The price is AU$281 per night from 7 May to 8 May
AU$281
includes taxes & fees
7 May - 8 May
With a stay at Inn on Storrs in Mansfield, you'll be in a state park, within a 10-minute drive of University of Connecticut and East Brook Mall.
Inn on Storrs
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Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$187 per night from 11 May to 12 May
AU$187
includes taxes & fees
11 May - 12 May
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.