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South Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for South Woodstock holiday rentals

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 HK$3,173
HK$5,371 total
includes taxes & fees
16 Jun - 17 Jun
Stunning Lakefront Escape! Book Your Dream Getaway!
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (31 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is HK$1,375
HK$2,017 total
includes taxes & fees
16 Jun - 17 Jun
Dove Cabin up in the Trees
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 HK$987
HK$1,472 total
includes taxes & fees
21 Jun - 22 Jun
Wizard's Roost at Underhill Hollow
Terrace/patio

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, (40 reviews)
"Very nice area."
United States
maureen p.
The price is HK$1,175
HK$2,791 total
includes taxes & fees
16 Jun - 17 Jun
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
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 HK$987
HK$1,525 total
includes taxes & fees
18 Jun - 19 Jun
The Tree House at Underhill Hollow
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.4 out of 10, Exceptional, (33 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$2,588
HK$4,301 total
includes taxes & fees
21 Jun - 22 Jun
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
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 HK$7,757
HK$13,899 total
includes taxes & fees
19 Jun - 20 Jun
Sleeps 15 • Pool • World Cup 2026 • Retreat
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 HK$1,305
HK$2,049 total
includes taxes & fees
23 Jun - 24 Jun
Spacious, unique barn with beautiful views.
Exterior

Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (34 reviews)
"The tree house matched the description perfectly! The host was very responsive, the house was clean, and the temperature was comfortable. All instructions were provided prior to our arrival and easy to understand. The manager was friendly and we loved spending time with the animals. It was a little pricey but I would stay again. Great getaway for my husband and i to connect with nature!"
United States
Pattie
The price is HK$1,439
HK$2,830 total
includes taxes & fees
22 Jun - 23 Jun
Treehouse - Countryside - Farm Animals - Fire Pit
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 HK$987
HK$1,472 total
includes taxes & fees
19 Jun - 20 Jun
SteamPunk Bunk House and Intergalactic Way Station
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
9.2 out of 10, Wonderful, (5 reviews)
"This is a nice place for solo travelers or a small family with kids. The kid’s bedroom has tons of games and is themed nicely. The backyard is huge but unfenced and the property is off of a busy road. Th house itself was clean and the host offered a variety of things such as slippers for the whole family, house shoes, and bath things for everyone. The house does not have a tv but the wifi works well. "
United States
Chantay-Rose
The price is HK$1,598
HK$1,996 total
includes taxes & fees
16 Jun - 17 Jun
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
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 HK$2,351
HK$2,967 total
includes taxes & fees
26 Jun - 27 Jun
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
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 HK$1,516
HK$2,903 total
includes taxes & fees
23 Jun - 24 Jun
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
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
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
Exterior

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.6 out of 10, Excellent, (4 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$1,079
HK$1,872 total
includes taxes & fees
16 Jun - 17 Jun
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
TV

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
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 HK$3,722
HK$6,080 total
includes taxes & fees
21 Jun - 22 Jun
Secluded 2-Acre Lakefront Home! Book Your Getaway!
2 bedrooms, desk, iron/ironing board, WiFi

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$776
HK$1,989 total
includes taxes & fees
21 Jun - 22 Jun
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (1 review)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
The price is HK$1,591
HK$2,993 total
includes taxes & fees
16 Jun - 17 Jun
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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

10/10 Excellent
"Loved it"
Jennifer 2-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:

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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.