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South Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for South Woodstock vacation rentals

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, (46 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is ￥19,865
￥30,531 total
includes taxes & fees
Nov 1 - Nov 2
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)
"Great stay!!"
United States
Elizabeth G.
The price is ￥19,865
￥29,624 total
includes taxes & fees
Nov 1 - Nov 2
Wizard's Roost at Underhill Hollow
A two-story house with a front porch, stone steps, and a driveway.

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
The price is ￥17,737
￥32,775 total
includes taxes & fees
Nov 2 - Nov 3
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
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.

4. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is ￥19,865
￥29,624 total
includes taxes & fees
Nov 4 - Nov 5
SteamPunk Bunk House and Intergalactic Way Station
A bedroom with a wooden bed, large windows, and a view of greenery outside.

5. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
The price is ￥39,415
￥60,541 total
includes taxes & fees
Nov 4 - Nov 5
Rustic Farmette Studio with Hot Tub & Pool
A house with a white porch, a black door, and a window with a white frame.

6. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.2 out of 10, Wonderful, (5 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 ￥33,897
￥43,396 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 1-bedroom cottage in serene Pomfret.
Surroundings [summer] (1-5 km)

7. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
10.0 out of 10, Exceptional, (4 reviews)
"Offers good value with cozy accommodations."
United States
Anonymous traveler
The price is ￥13,827
￥15,900 total
includes taxes & fees
Nov 1 - Nov 2
1 King Bed | Non-Smoking, Micfridge
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (95 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is ￥59,123
￥101,218 total
includes taxes & fees
Nov 4 - Nov 5
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A modern interior with a kitchen, dining area, and living space.

9. 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, (2 reviews)
"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 ￥28,615
￥91,228 total
includes taxes & fees
Nov 1 - Nov 2
6 Beds Home w/Game Room Perfect for Groups
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
6.0 out of 10, (3 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is ￥14,978
￥20,253 total
includes taxes & fees
Nov 1 - Nov 2
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (23 reviews)
"The place was unique and cozy. The hosts were very friendly and our stay was great"
United States
Stacy
The price is ￥12,991
￥35,278 total
includes taxes & fees
Nov 3 - Nov 4
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A lakeside cabin with a deck, a dock, and a small docked boat.

12. 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
9.8 out of 10, Exceptional, (98 reviews)
"very clean, wonderful location"
United States
Anonymous traveler
The price is ￥35,474
￥74,495 total
includes taxes & fees
Nov 2 - Nov 3
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A wooden cabin with a glass upper floor, surrounded by a forest.

13. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful cabin wishing it was a waterfront"
United States
Magdalena W.
The price is ￥27,669
￥40,578 total
includes taxes & fees
Oct 31 - Nov 1
Dove Cabin up in the Trees
A window with a view of a grassy field and trees.

14. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (8 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 ￥31,217
￥45,990 total
includes taxes & fees
Nov 2 - Nov 3
Spacious, unique barn with beautiful views.
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

15. Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.

Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
Stafford
9.6 out of 10, Exceptional, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
The price is ￥18,919
￥49,466 total
includes taxes & fees
Nov 10 - Nov 11
Serene 2-bedroom, 2-bath lakefront retreat on Staffordville Lake for 5 people.
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (25 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 ￥44,145
￥117,648 total
includes taxes & fees
Nov 1 - Nov 2
Lake House in Sturbridge w/All the Views!
A wooden cabin with a balcony and stairs, surrounded by trees.

17. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful treehouse with everything you need. My kids loved picking blueberries and meeting the farm animals!"
United States
Lauren B.
The price is ￥12,613
￥36,262 total
includes taxes & fees
Nov 1 - Nov 2
Treehouse - Countryside - Farm Animals - Fire Pit
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

18. 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, (12 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 ￥25,541
￥32,227 total
includes taxes & fees
Nov 2 - Nov 3
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

19. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (4 reviews)
"Gorgeously decorated and ultra-clean. Was the perfect rental for my sisters wedding at Salem Cross Inn"
United States
Trish N.
The price is ￥23,649
￥49,661 total
includes taxes & fees
Nov 29 - Nov 30
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A two-story house with a porch, a flag, and potted plants.

20. The Little Blue Bird · 5 Mi UConn · 2 Min I-84

The Little Blue Bird · 5 Mi UConn · 2 Min I-84
Willington
10.0 out of 10, Exceptional, (2 reviews)
"Great place! Great communication! Highly recommended for 1-2 people."
United States
Jeff G.
The price is ￥15,031
￥25,878 total
includes taxes & fees
Nov 9 - Nov 10
The Little Blue Bird · 5 Mi UConn · 2 Min I-84
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

Sturbridge Host Hotel & Conference Center

Sturbridge Host Hotel & Conference Center

8/10 Good
"The hotel is quite large There are entertainment areas that are closed No breakfast services available It appears that in previous years it was a wonderful place The rooms are large but the carpet and paint are in need of improvement It is just across the Sturbridge village"
Luis 2-night trip
Posted 1 hour ago
Sturbridge Host Hotel & Conference Center

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:

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

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 Quaddick Reservoir. 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.