Default HTG hotel image

South Woodstock Holiday Rentals

  • 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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for South Woodstock holiday rentals

Terrace/patio

1. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"Great experience. Thank you "
United States
edmund d.
The price is HK$3,529
HK$5,813 total
includes taxes & fees
7 Aug - 8 Aug
Stunning Lakefront Escape! Book Your Dream Getaway!
Interior

2. 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 HK$988
HK$1,519 total
includes taxes & fees
3 Aug - 4 Aug
The Tree House at Underhill Hollow
Exterior detail

3. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$1,921
HK$2,461 total
includes taxes & fees
3 Aug - 4 Aug
Cozy 1-bedroom cottage in serene Pomfret.
Property grounds

4. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
The price is HK$988
HK$1,474 total
includes taxes & fees
2 Aug - 3 Aug
SteamPunk Bunk House and Intergalactic Way Station
Exterior

5. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 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 HK$988
HK$1,474 total
includes taxes & fees
13 Aug - 14 Aug
Wizard's Roost at Underhill Hollow
Exterior

6. Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (5 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
The price is HK$1,249
HK$2,099 total
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Interior

7. Quintessential New England Home w/ Patio & Grill!

Quintessential New England Home w/ Patio & Grill!
3.0 star property
Putnam
Quintessential New England Home w/ Patio & Grill!
Dining

8. 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 HK$3,922
HK$6,312 total
includes taxes & fees
30 Aug - 31 Aug
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

9. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
8.0 out of 10, Very good, (1 review)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is HK$463
HK$692 total
includes taxes & fees
8 Aug - 9 Aug
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Exterior

10. The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
The price is HK$863
HK$1,608 total
includes taxes & fees
26 Aug - 27 Aug
The Carriage House at Chaprae Hall
Interior

11. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (5 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 HK$1,306
HK$2,074 total
includes taxes & fees
2 Aug - 3 Aug
Spacious, unique barn with beautiful views.
Property grounds

12. Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.8 out of 10, Exceptional, (16 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
The price is HK$665
HK$1,824 total
includes taxes & fees
3 Aug - 4 Aug
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Exterior

13. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (32 reviews)
"Sue is a great host, making necessary adjustments to suit the circumstances, generous and flexible. The dove cabin is so sweet, comfortable beds, cozy stove and fully equipped kitchen. And lovely porch! There’s a really cool swing on the way down to a peaceful pond!"
United States
kathryn m.
The price is HK$1,376
HK$2,018 total
includes taxes & fees
12 Aug - 13 Aug
Dove Cabin up in the Trees
TV

14. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
6 Beds Home w/Game Room Perfect for Groups
Exterior

15. Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (36 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
The price is HK$1,680
HK$3,116 total
includes taxes & fees
5 Aug - 6 Aug
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Smart TV

16. Serenity meets Taradise

Serenity meets Taradise
Union
The price is HK$847
HK$1,356 total
includes taxes & fees
2 Aug - 3 Aug
Serenity meets Taradise
Interior

17. Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is HK$471
HK$1,130 total
includes taxes & fees
7 Aug - 8 Aug
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Coffee/tea maker, fridge, microwave, oven

18. 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.
Mohegan Sun Getaway Large Group Retreat
Outdoor dining

19. 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 HK$2,315
HK$3,964 total
includes taxes & fees
13 Aug - 14 Aug
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
TV, fireplace

20. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (37 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 HK$7,647
HK$13,763 total
includes taxes & fees
31 Aug - 1 Sept
Sleeps 15 • Pool • Retreat
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Everything about this place and our stay was fantastic! Super friendly staff & evening manager is very engaging. Dinner & drinks in the restaurant was top notch. Highly recommend!"
Laurie 1-night trip
Posted 7 hours ago
Wellsworth Hotel

Find out more about South Woodstock

Search for holiday rentals in South Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in South Woodstock using one of the methods below:

  • View our selection of featured holiday rentals in South Woodstock
  • Use the map to find apartments and other holiday homes in the South Woodstock neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Woodstock while they last

Look no further and take a look at our great range of rental properties in South Woodstock!

Frequently asked questions

Are there holiday rentals in South Woodstock?

Yes, there are holiday rentals close to the most popular sights in South Woodstock, or you can select a more secluded option if you're looking for a relaxing stay. South Woodstock is known for its golf courses and shopping.

What are some of the best holiday rentals that South Woodstock has to offer?

Stunning Lakefront Escape! Book Your Dream Getaway!: This highly rated holiday home rental in South Woodstock is located on the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in South Woodstock?

Explore the area and family-friendly sights such as Mohegan Bowl, or get out into nature at a spot like Black Pond. Little River Plaza Shopping Center and Harrisville Golf Course are other places to visit while you're in town.

What’s a holiday rental in South Woodstock like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Woodstock. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.