Holiday Homes in Woodstock

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Woodstock holiday homes

Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (24 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is €636
includes taxes & fees
31 May - 1 Jun
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (84 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is €664
includes taxes & fees
31 May - 1 Jun
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (22 reviews)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is €165
includes taxes & fees
31 May - 1 Jun
Wizard's Roost at Underhill Hollow
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
The price is €228
includes taxes & fees
1 Jun - 2 Jun
Spacious, unique barn with beautiful views.
Sailing, kayaking, fishing

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut

Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Stafford Springs
The price is €205
includes taxes & fees
31 May - 1 Jun
Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
Interior

Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (40 reviews)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is €259
includes taxes & fees
1 Jun - 2 Jun
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (37 reviews)
"Such a fun getaway!"
United States
Patrice D.
The price is €170
includes taxes & fees
2 Jun - 3 Jun
The Tree House at Underhill Hollow
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is €165
includes taxes & fees
31 May - 1 Jun
SteamPunk Bunk House and Intergalactic Way Station
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (21 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
The price is €244
includes taxes & fees
1 Jun - 2 Jun
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Books

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Brimfield
8.8 out of 10, Excellent, (3 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is €198
includes taxes & fees
1 Jun - 2 Jun
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Dining

Beautiful Worcester Downtown King Bd/Office World Cup Boston

Beautiful Worcester Downtown King Bd/Office World Cup Boston
Worcester
10.0 out of 10, Exceptional, (1 review)
"I had an amazing stay here and would absolutely recommend this place to anyone visiting Boston or Worcester, Massachusetts. The house was truly 100% excellent. Everything was incredibly clean, spacious, and well organized. I loved the kitchen, my room, and the bathroom, everything was spotless and very comfortable. Honestly, the entire home was sparkling clean and very welcoming.I also slept extremely well during my stay. The bed, pillows, and bedding were so comfortable, which made the...
United States
Masard T.
The price is €360
includes taxes & fees
9 Jun - 10 Jun
Beautiful Worcester Downtown King Bd/Office World Cup Boston
Interior

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Windham
10.0 out of 10, Exceptional, (14 reviews)
"All and all a great place to stay."
United States
Anonymous traveller
The price is €594
includes taxes & fees
15 Jun - 16 Jun
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Exterior

Cottage by the Castle – Downtown Spencer

Cottage by the Castle – Downtown Spencer
Spencer
The price is €165
includes taxes & fees
31 May - 1 Jun
Cottage by the Castle – Downtown Spencer
Fridge, microwave, oven, coffee/tea maker

Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
"Great setup. Perfect crash pad for a weekend of the Natchaug Epic bike race in Thompson… slept 8 no problem. Host was helpful and beds were clean, kitchens were just what we needed"
United States
shawn c b.
The price is €596
includes taxes & fees
31 May - 1 Jun
Mohegan Sun Getaway Large Group Retreat
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"10/10 great place to stay"
United States
Tyler B.
The price is €434
includes taxes & fees
1 Jun - 2 Jun
Spacious 4-bedroom with four and half bathrooms
Property grounds

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
The price is €320
includes taxes & fees
9 Jun - 10 Jun
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Dining

Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
The price is €405
includes taxes & fees
29 Jun - 30 Jun
Clifford Luxury Retreat 3BR Self Check In Home
TV, fireplace

Sleeps 15 • Pool • World Cup 2026 • Retreat

Sleeps 15 • Pool • World Cup 2026 • Retreat
Brimfield
10.0 out of 10, Exceptional, (34 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is €1,510
includes taxes & fees
1 Jun - 2 Jun
Sleeps 15 • Pool • World Cup 2026 • Retreat
Interior

Cozy 3-bedroom house in serene Worcester with fitness room and office

Cozy 3-bedroom house in serene Worcester with fitness room and office
Worcester
The price is €508
includes taxes & fees
31 May - 1 Jun
Cozy 3-bedroom house in serene Worcester with fitness room and office
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (21 reviews)
"Thank you for a wonderful stay! Our family enjoyed the gorgeous views and the well-equipped home. There were toys, books, and games for the kids, and the beds were very comfortable. We’d definitely stay again!"
United States
Caitlin D.
The price is €819
includes taxes & fees
31 May - 1 Jun
Lake House in Sturbridge w/All the Views!
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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Top Woodstock Hotel Reviews

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"Went there for a wedding, so only 1 night. Staff was great. It’s a historic inn, so older. Stayed in the motor lodge portion which also has an older feel. I think that is expected. Everything was clean and in good shape. Food was excellent"
Brian 1-night trip
Posted 3 hours ago
Publick House Historic Inn and Country Motor Lodge

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
338
Accommodation
92 Holiday Homes
Lowest Price
€165
Highest Price
€1,510