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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for South Woodstock holiday homes

A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

1. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (44 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is £149
includes taxes & fees
8 Oct - 9 Oct
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

2. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
The price is £145
includes taxes & fees
8 Oct - 9 Oct
Wizard's Roost at Underhill Hollow
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

3. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is £145
includes taxes & fees
8 Oct - 9 Oct
SteamPunk Bunk House and Intergalactic Way Station
A modern interior with a kitchen, dining area, and living space.

4. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
10.0 out of 10, Exceptional, (1 review)
"Edgar was very responsive and easy to work with. The unit was very clean and well kept. I would definitely stay there again."
United States
debra l.
The price is £441
includes taxes & fees
8 Oct - 9 Oct
6 Beds Home w/Game Room Perfect for Groups
A dining area with a high ceiling, skylights, and a view of the outdoors.

5. Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is £482
includes taxes & fees
1 Nov - 2 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A window with a view of a grassy field and trees.

6. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (7 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 £232
includes taxes & fees
11 Oct - 12 Oct
Spacious, unique barn with beautiful views.
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

7. 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
9.2 out of 10, Wonderful, (10 reviews)
"What a beautiful set up for a pet friendly family stay - candles lit upon arrival and a child’s room filled with toys ready to be enjoyed."
United States
Gregory C.
The price is £172
includes taxes & fees
13 Oct - 14 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

8. 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 £471
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

9. Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 reviews)
"Pictures don't do this house justice! Great communication from start to finish, very clean house & property, coolest house we've ever stayed at. Hope to stay again!"
United States
Mike T.
The price is £646
includes taxes & fees
12 Oct - 13 Oct
Lake House in Sturbridge w/All the Views!
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

10. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Webster
10.0 out of 10, Exceptional, (3 reviews)
"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."
United States
Kyle C.
The price is £669
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
A spacious living room with a large sectional sofa, wooden flooring, and a high ceiling with skylights.

11. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (39 reviews)
"It was a beautiful property. Well-tended and all the amenities. Loved the view in morning and evening of mountains and sun / moon."
United States
Daniel C.
The price is £1,315
includes taxes & fees
9 Oct - 10 Oct
Sleeps 15 • Pool • Retreat
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

12. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.6 out of 10, Excellent, (7 reviews)
The price is £400
includes taxes & fees
12 Oct - 13 Oct
Clifford Luxury Retreat 3BR Self Check In Home
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 South Woodstock Hotel Reviews

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"All staff were amazingly personal and helpful, low staffing in dining room resulted in food delivered just warm not hot and long delays for food delivery. The only waitress was efficient and apologetic and very sweet. Establishment was great, food good but entrees not hot, room extensive and bake shop with coffee in am free with room was amazing!! Will be back!"
Deborah 1-night trip
Posted 20 hours ago
Publick House Historic Inn and Country Motor Lodge

Find out more about South Woodstock

South Woodstock Holiday Homes information

Number of reviews
277
Accommodation
45 Holiday Homes
Lowest Price
£145
Highest Price
£1,315