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Holiday Homes in South Woodstock

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Check prices for these dates

In two weeks
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for South 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, (26 reviews)
"Great experience. Thank you "
United States
edmund d.
The price is AU$1,041
includes taxes & fees
26 July - 27 July
Stunning Lakefront Escape! Book Your Dream Getaway!
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is AU$280
includes taxes & fees
21 July - 22 July
The Tree House at Underhill Hollow
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (23 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 AU$271
includes taxes & fees
22 July - 23 July
Wizard's Roost 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, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AU$294
includes taxes & fees
2 Aug - 3 Aug
SteamPunk Bunk House and Intergalactic Way Station
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (4 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 AU$379
includes taxes & fees
20 July - 21 July
Spacious, unique barn with beautiful views.
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is AU$1,008
includes taxes & fees
19 July - 20 July
6 Beds Home w/Game Room Perfect for Groups
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, (22 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 AU$528
includes taxes & fees
19 July - 20 July
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
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 AU$529
includes taxes & fees
26 July - 27 July
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (87 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AU$1,095
includes taxes & fees
19 July - 20 July
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Property grounds

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, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is AU$360
includes taxes & fees
12 Aug - 13 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Interior

Lake House in Sturbridge w/All the Views!

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (22 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 AU$1,307
includes taxes & fees
29 July - 30 July
Lake House in Sturbridge w/All the Views!
Property grounds

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 AU$924
includes taxes & fees
26 July - 27 July
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
TV, fireplace

Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (36 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 AU$2,230
includes taxes & fees
30 July - 31 July
Sleeps 15 • Pool • Retreat
3 bedrooms, desk, iron/ironing board, free WiFi

Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
The price is AU$638
includes taxes & fees
23 July - 24 July
Clifford Luxury Retreat 3BR Self Check In Home
Property grounds

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
10.0 out of 10, Exceptional, (94 reviews)
"Amazing place to gather and relax. "
United States
Evan M.
The price is AU$1,522
includes taxes & fees
9 Aug - 10 Aug
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
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

8/10 Good
"Publick house is an historic inn with a newer addition and a 1960's era motor lodge on its grounds. Since we were visiting the Brimfield Antiques market we only needed to stay in the motor lodge . It was extremely comfortable with nice linens and beds . We asked for maid service one day and it was done spotlessly. The food in the restaurant is quite good and they give free coffee and pastries in the Bake shop every morning. There's a refreshing pool as well"
Phillip 4-night trip
Posted 7 hours ago
Publick House Historic Inn and Country Motor Lodge

Find out more about South Woodstock

South Woodstock Holiday Homes information

Number of reviews
362
Accommodation
57 Holiday Homes
Lowest Price
AU$271
Highest Price
AU$2,230