Book Holiday Homes in Woodstock Valley

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Featured Holiday Homes in Woodstock Valley

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!
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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 24 Dec to 25 Dec
AU$1,538
includes taxes & fees
24 Dec - 25 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
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
The Lake House

The Lake House

Coventry
With a stay at this vacation home in Coventry (Coventry Lake), you'll be within a 10-minute drive of University of Connecticut and J. M. Sarnik & Sons' The Old ...
The Lake House
Beautiful lake front home. Amazing view!

Beautiful lake front home. Amazing view!

Ashford
Located in Ashford, this vacation home is on a lake, within a 15-minute drive of Tinkerville Brook Reserve and Bigelow Hollow State Park.
Beautiful lake front home. Amazing view!
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See all available properties in Woodstock Valley
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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 Valley 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 Valley vacation homes are the perfect way for you to wing it.

Holiday houses in Woodstock Valley 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 Valley 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 Valley adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Woodstock Valley 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 Valley 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 Valley Holiday Homes essential information

Accommodation
52 Holiday Homes
Lowest Price
AU$116
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, 5 bedrooms Home away from Home , The Lake House, Beautiful lake front home. Amazing view!

Top trending hotels in Woodstock Valley

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
Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131), Sturbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 24 Dec to 25 Dec
AU$141
includes taxes & fees
24 Dec - 25 Dec
When you stay at Publick House Historic Inn and Country Motor Lodge in Sturbridge, you'll be in the historical district, within a 5-minute drive of Old Sturbridge ...
Publick House Historic Inn and Country Motor Lodge
Days Inn by Wyndham Sturbridge

Days Inn by Wyndham Sturbridge

2 out of 5
400 Haynes St., Route 15, Sturbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$116 per night from 24 Dec to 25 Dec
AU$116
includes taxes & fees
24 Dec - 25 Dec
With a stay at Days Inn by Wyndham Sturbridge in Sturbridge, you'll be within a 10-minute drive of Old Sturbridge Village and Leadmine Wildlife Management ...
Days Inn by Wyndham Sturbridge
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Holiday Inn Express Hotel & Suites Auburn, an IHG Hotel

Holiday Inn Express Hotel & Suites Auburn, an IHG Hotel

2.5 out of 5
10-12 Johnson St, Auburn, MA
Fully refundable
The price is AU$181 per night from 29 Dec to 30 Dec
AU$181
includes taxes & fees
29 Dec - 30 Dec
Located in Auburn, Holiday Inn Express Hotel & Suites Auburn, an IHG Hotel is within a 10-minute drive of College of the Holy Cross and The Hanover Theatre for ...
Holiday Inn Express Hotel & Suites Auburn, an IHG Hotel
Don't see what you're looking for?
See all available properties in Woodstock Valley
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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.

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^Subject to availability and chosen travel dates.