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South Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for South Woodstock vacation 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 ￥70,830
￥116,673 total
includes taxes & fees
Aug 5 - Aug 6
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 ￥19,832
￥30,480 total
includes taxes & fees
Aug 7 - Aug 8
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)
"I had a lovely stay at the cottage! It was clean, comfortable, and quiet with a great view. The hosts were very helpful."
United States
Aaron H.
The price is ￥38,563
￥49,384 total
includes taxes & fees
Aug 4 - Aug 5
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)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is ￥19,832
￥29,575 total
includes taxes & fees
Aug 4 - Aug 5
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 ￥19,832
￥29,575 total
includes taxes & fees
Aug 14 - Aug 15
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 ￥23,799
￥40,512 total
includes taxes & fees
Sep 1 - Sep 2
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
House (5 Bedrooms) | Interior

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

Quintessential New England Home w/ Patio & Grill!
3.0 star property
Putnam
The price is ￥60,284
￥142,398 total
includes taxes & fees
Aug 9 - Aug 10
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 ￥74,765
￥121,670 total
includes taxes & fees
Aug 5 - Aug 6
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 ￥11,805
￥16,703 total
includes taxes & fees
Aug 11 - Aug 12
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 ￥17,314
￥32,267 total
includes taxes & fees
Aug 26 - Aug 27
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 ￥26,207
￥41,629 total
includes taxes & fees
Aug 6 - Aug 7
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 ￥13,379
￥37,264 total
includes taxes & fees
Sep 1 - Sep 2
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 ￥27,624
￥40,512 total
includes taxes & fees
Aug 4 - Aug 5
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
The price is ￥30,300
￥110,179 total
includes taxes & fees
Aug 4 - Aug 5
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 ￥31,354
￥58,251 total
includes taxes & fees
Aug 5 - Aug 6
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Smart TV

16. Serenity meets Taradise

Serenity meets Taradise
Union
The price is ￥16,999
￥27,222 total
includes taxes & fees
Aug 10 - Aug 11
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 ￥9,444
￥22,680 total
includes taxes & fees
Aug 7 - Aug 8
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.
The price is ￥30,063
￥109,734 total
includes taxes & fees
Aug 4 - Aug 5
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 ￥35,289
￥65,294 total
includes taxes & fees
Aug 18 - Aug 19
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 ￥138,119
￥256,603 total
includes taxes & fees
Sep 1 - Sep 2
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.
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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
"It feels like a hallmark movie! Super clean rooms, dated but very nice. Would stay again!"
Kallie 1-night trip
Posted 11 hours ago
Publick House Historic Inn and Country Motor Lodge

Find out more about South Woodstock

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Frequently asked questions

Are there vacation rentals in South Woodstock?

Yes, you can find vacation rentals near top sights in South Woodstock, or you can go with a more remote option if you're looking for relaxation. South Woodstock is known for its golf courses and shopping.

What are some of the best vacation home rentals in South Woodstock?

Stunning Lakefront Escape! Book Your Dream Getaway!: Visitors give good reviews to this South Woodstock vacation home rental, which is located on the beach and has a patio, a selection of games, and a barbecue grill 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 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 vacation rental in South Woodstock like?

Vacation rentals are privately owned properties you can stay in for a long or short time in South Woodstock. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for small groups.