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South Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for South Woodstock vacation rentals

A red building with a colorful mural on the front, a covered porch, and a stone foundation.

1. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 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 AED 463
AED 690 total
includes taxes & fees
2 Oct - 3 Oct
Wizard's Roost at Underhill Hollow
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

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 AED 463
AED 711 total
includes taxes & fees
4 Oct - 5 Oct
The Tree House 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 AED 446
AED 805 total
includes taxes & fees
6 Oct - 7 Oct
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, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AED 463
AED 690 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 918
AED 1,410 total
includes taxes & fees
5 Oct - 6 Oct
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
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
The price is AED 900
AED 1,152 total
includes taxes & fees
14 Oct - 15 Oct
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
The price is AED 326
AED 375 total
includes taxes & fees
2 Oct - 3 Oct
1 King Bed | Non-Smoking, Micfridge
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is AED 349
AED 673 total
includes taxes & fees
12 Oct - 13 Oct
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

9. 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 AED 680
AED 2,145 total
includes taxes & fees
4 Oct - 5 Oct
Mohegan Sun Getaway Large Group Retreat
A window with a view of a grassy field and trees.

10. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (7 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 AED 727
AED 1,119 total
includes taxes & fees
4 Oct - 5 Oct
Spacious, unique barn with beautiful views.
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

11. 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 AED 1,837
AED 2,314 total
includes taxes & fees
14 Oct - 15 Oct
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is AED 1,377
AED 2,365 total
includes taxes & fees
1 Nov - 2 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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, (36 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is AED 645
AED 945 total
includes taxes & fees
4 Oct - 5 Oct
Dove Cabin up in the Trees
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (19 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 AED 335
AED 899 total
includes taxes & fees
18 Oct - 19 Oct
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

15. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"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 AED 551
AED 1,157 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

16. 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 AED 474
AED 1,190 total
includes taxes & fees
6 Oct - 7 Oct
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A spacious deck with wicker furniture, large windows offering a view of a lake and trees, and a wooden ceiling.

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

Lake House in Sturbridge w/All the Views!
Sturbridge
9.6 out of 10, Exceptional, (24 reviews)
"We really appreciated the kindling and firewood for the outdoor fire pit.The house was clean and nice."
United States
Christian C.
Lake House in Sturbridge w/All the Views!
A wooden cabin with a balcony and stairs, surrounded by trees.

18. 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 AED 613
AED 1,253 total
includes taxes & fees
20 Oct - 21 Oct
Treehouse - Countryside - Farm Animals - Fire Pit
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

19. 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, (10 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 AED 582
AED 736 total
includes taxes & fees
5 Oct - 6 Oct
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A cozy attic bedroom with a skylight, a piano, a mirror, and a bedside table with a lamp.

20. Clifford Luxury Retreat 3BR Self Check In Home

Clifford Luxury Retreat 3BR Self Check In Home
Northbridge
8.6 out of 10, Excellent, (7 reviews)
The price is AED 1,653
AED 1,988 total
includes taxes & fees
2 Oct - 3 Oct
Clifford Luxury Retreat 3BR Self Check In Home
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

Fairfield Inn & Suites by Marriott Worcester Auburn

Fairfield Inn & Suites by Marriott Worcester Auburn

10/10 Excellent
"Good"
francisco 4-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott Worcester Auburn

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.