Holiday Homes in South Woodstock

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 June - 21 June
In two months
31 July - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

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, (25 reviews)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is AU$1,034
includes taxes & fees
3 June - 4 June
Stunning Lakefront Escape! Book Your Dream 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 AU$264
includes taxes & fees
3 June - 4 June
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 AU$370
includes taxes & fees
4 June - 5 June
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 AU$329
includes taxes & fees
3 June - 4 June
Wonderful Suite In a Charming Bed and Breakfast for a Weekend Getaway near Shenipsit State Forest, Connecticut
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 AU$272
includes taxes & fees
3 June - 4 June
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 AU$264
includes taxes & fees
3 June - 4 June
SteamPunk Bunk House and Intergalactic Way Station
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, (15 reviews)
"All and all a great place to stay."
United States
Anonymous traveller
The price is AU$934
includes taxes & fees
15 June - 16 June
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
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
8.8 out of 10, Excellent, (3 reviews)
"Excellent communicative host with warm welcome and delightful amenities. Quiet neighborhood with plenty of parking."
United States
Pamela L.
The price is AU$326
includes taxes & fees
8 June - 9 June
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
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 AU$495
includes taxes & fees
8 June - 9 June
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
The price is AU$953
includes taxes & fees
7 June - 8 June
6 Beds Home w/Game Room Perfect for Groups
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$519
includes taxes & fees
9 June - 10 June
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 AU$675
includes taxes & fees
3 June - 4 June
Clifford Luxury Retreat 3BR Self Check In Home
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 AU$1,069
includes taxes & fees
3 June - 4 June
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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 AU$2,429
includes taxes & fees
4 June - 5 June
Sleeps 15 • Pool • World Cup 2026 • Retreat
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 AU$1,165
includes taxes & fees
3 June - 4 June
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$763
includes taxes & fees
26 June - 27 June
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Woodstock Hotel Reviews

Graduate by Hilton Storrs

Graduate by Hilton Storrs

10/10 Excellent
"Overall, the hotel, room, and staff were very good. The hotel furniture inside the rooms could usesome sprucing up since it shows a lot of dings and bruises. The beds were comfortable and room was a good temperature that could be adjusted. Though we did not use the bikes, we love the idea that bikes were available to use to reach the campus and community. The only issue was that we would.have liked to have eaten on the premises the first night but the restaurant was not open and there was no menu to see if we could eat breakfast on the premises."
Lara 2-night trip
Posted 2 hours ago
Graduate by Hilton Storrs

Find out more about South Woodstock

South Woodstock Holiday Homes information

Number of reviews
287
Accommodation
57 Holiday Homes
Lowest Price
AU$264
Highest Price
AU$2,429