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South Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

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, (28 reviews)
"We loved our stay at this lakeside retreat. We were in town for a wedding and in between family gatherings we were able to relax by the lake. The house was comfortable and well stocked so we didn't have to buy every little thing. I would definitely stay again"
United States
Lisa R.
The price is HK$3,529
HK$5,813 total
includes taxes & fees
26 Sept - 27 Sept
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, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is HK$988
HK$1,519 total
includes taxes & fees
15 Sept - 16 Sept
The Tree House at Underhill Hollow
Exterior

3. 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
15 Sept - 16 Sept
Wizard's Roost at Underhill Hollow
Property grounds

4. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is HK$988
HK$1,474 total
includes taxes & fees
15 Sept - 16 Sept
SteamPunk Bunk House and Intergalactic Way Station
Exterior

5. 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, (6 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$1,094
HK$1,850 total
includes taxes & fees
22 Sept - 23 Sept
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior detail

6. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
8.8 out of 10, Excellent, (3 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 HK$1,921
HK$2,476 total
includes taxes & fees
15 Sept - 16 Sept
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (39 reviews)
"We had a nice stay in this cabin by the lake. It was close to UCONN so the convenience of the location was wonderful. "
United States
Jennifer P.
The price is HK$828
HK$2,058 total
includes taxes & fees
15 Sept - 16 Sept
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Property grounds

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (18 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$533
HK$1,672 total
includes taxes & fees
16 Sept - 17 Sept
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is HK$392
HK$1,042 total
includes taxes & fees
16 Sept - 17 Sept
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Exterior

10. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Beautiful farm that’s perfect little getaway for one weekend"
United States
Justyn M.
The price is HK$822
HK$2,051 total
includes taxes & fees
17 Sept - 18 Sept
Treehouse - Countryside - Farm Animals - Fire Pit
Exterior

11. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is HK$1,376
HK$2,027 total
includes taxes & fees
15 Sept - 16 Sept
Dove Cabin up in the Trees
Terrace/patio

12. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
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 HK$1,020
HK$2,574 total
includes taxes & fees
20 Sept - 21 Sept
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Living area

13. Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat

Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Holland
10.0 out of 10, Exceptional, (1 review)
"Cute place! Susan was a great host and the cabin was perfect for a qick getaway weekend and some reconnection with mother nature.."
United States
Jessica K.
The price is HK$1,341
HK$1,907 total
includes taxes & fees
17 Sept - 18 Sept
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Interior

14. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (6 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$1,553
HK$2,382 total
includes taxes & fees
16 Sept - 17 Sept
Spacious, unique barn with beautiful views.
Private kitchen

15. 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
Living area

16. 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
Property grounds

17. 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, (9 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 HK$1,098
HK$1,402 total
includes taxes & fees
15 Sept - 16 Sept
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Outdoor dining

18. Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (24 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is HK$1,162
HK$2,489 total
includes taxes & fees
24 Sept - 25 Sept
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (89 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$3,725
HK$6,078 total
includes taxes & fees
17 Sept - 18 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Exterior detail

20. Cozy apartment in quiet setting that is very convenient to UConn and ECSU.

Cozy apartment in quiet setting that is very convenient to UConn and ECSU.
Mansfield
9.4 out of 10, Exceptional, (3 reviews)
"Super nice place, owners live near the property and are super super nice and accommodating. Great area, very convenient place to get some shuteye in a lovely setting! 5 Stars!"
United States
Owen M.
The price is HK$1,114
HK$2,200 total
includes taxes & fees
16 Sept - 17 Sept
Cozy apartment in quiet setting that is very convenient to UConn and ECSU.
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

Wellsworth Hotel

Wellsworth Hotel

8/10 Good
"The hotel was built in a former optical factory and the exterior is quite unique and beautiful. Unfortunately the interior seems to have lost most of its charm during this transformation and it generally felt a bit dated (very early 2000s vibe) and perhaps a bit past its heyday. That being said, the staff was pleasant, it seemed fairly well maintained and clean, and the pool and fitness center were nice amenities. It is also only a 25-30 minute drive to Brimfield, so a nice location if you’re coming to the antique market."
Laura 4-night trip
Posted 6 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:

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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 Breezy Picnic Grounds & Waterslides, 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 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.