Book Holiday Homes in Woodstock

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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
The price is AU$804 per night from 6 Apr to 7 Apr
AU$804
includes taxes & fees
6 Apr - 7 Apr
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!
Save an average of 15% on thousands of hotels when you're signed in
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$574 per night from 5 May to 6 May
AU$574
includes taxes & fees
5 May - 6 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
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$1,021 per night from 5 Apr to 6 Apr
AU$1,021
includes taxes & fees
5 Apr - 6 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!
Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!

Sturbridge
The price is AU$1,147 per night from 6 Apr to 7 Apr
AU$1,147
includes taxes & fees
6 Apr - 7 Apr
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!
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.

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$167
Highest Price
AU$1,147
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, Stunning Lakefront Escape! Exclusive Off-Season Rates – Book Your Dream Getaway!, Lake House in Sturbridge w/All the Views!

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$1,021 per night from 18 Apr to 19 Apr
AU$1,021
includes taxes & fees
18 Apr - 19 Apr
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$1,021 per night from 5 Apr to 6 Apr
AU$1,021
includes taxes & fees
5 Apr - 6 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!
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$189 per night from 20 Apr to 21 Apr
AU$189
includes taxes & fees
20 Apr - 21 Apr
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
Save an average of 15% on thousands of hotels when you're signed in
Comfort Inn Auburn - Worcester

Comfort Inn Auburn - Worcester

2.5 out of 5
426 Southbridge St, Auburn, MA
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 6 Apr to 7 Apr
AU$167
includes taxes & fees
6 Apr - 7 Apr
With a stay at Comfort Inn Auburn - Worcester in Auburn, you'll be within a 10-minute drive of DCU Center and Auburn Mall.
Comfort Inn Auburn - Worcester
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.