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South Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (42 reviews)
"Great space, lots of fun."
United States
Douglas C.
$171 nightly
The price is $194
Sep 27 - Sep 28
Total with taxes and fees
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)
"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.
$166 nightly
The price is $188
Sep 27 - Sep 28
Total with taxes and fees
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)
"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.
$194 nightly
The price is $220
Sep 27 - Sep 28
Total with taxes and fees
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.
$166 nightly
The price is $188
Sep 27 - Sep 28
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
A house with a white porch, a black door, and a window with a white frame.

5. 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.
$265 nightly
The price is $302
Sep 27 - Sep 28
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
A bedroom with a wooden bed, large windows, and a view of greenery outside.

6. 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.
$320 nightly
The price is $365
Sep 27 - Sep 28
Total with taxes and fees
Rustic Farmette Studio with Hot Tub & Pool
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

7. 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
$204 nightly
The price is $232
Sep 27 - Sep 28
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

8. 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.
$115 nightly
The price is $128
Sep 27 - Sep 28
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

9. 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
$267 nightly
The price is $304
Sep 28 - Sep 29
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A small, single-story cabin with a porch and a small deck, surrounded by trees and a lake.

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (40 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.
$275 nightly
The price is $313
Sep 30 - Oct 1
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
A wooden cabin with a balcony and stairs, surrounded by trees.

11. 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.
$269 nightly
The price is $306
Sep 27 - Sep 28
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
A wooden cabin with a glass upper floor, surrounded by a forest.

12. 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
$236 nightly
The price is $249
Sep 27 - Sep 28
Total with taxes and fees
Dove Cabin up in the Trees
A deck with red Adirondack chairs, a grill, and a view of trees and sunset.

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (25 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
$283 nightly
The price is $323
Sep 28 - Sep 29
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
A modern kitchen with white cabinetry, a wooden island, and a built-in stove.

14. 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.
$452 nightly
The price is $543
Sep 27 - Sep 28
Total with taxes and fees
Mohegan Sun Getaway Large Group Retreat
A modern interior with a kitchen, dining area, and living space.

15. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
$472 nightly
The price is $566
Sep 28 - Sep 29
Total with taxes and fees
6 Beds Home w/Game Room Perfect for Groups
A bedroom with a bed, a bedside table with a lamp, a window with curtains, a painting on the wall, and a carpet with a geometric pattern.

16. 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.
$221 nightly
The price is $234
Sep 27 - Sep 28
Total with taxes and fees
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
A window with a view of a grassy field and trees.

17. 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.
$258 nightly
The price is $294
Sep 29 - Sep 30
Total with taxes and fees
Spacious, unique barn with beautiful views.
A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (92 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$642 nightly
The price is $732
Sep 27 - Sep 28
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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, (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.
$170 nightly
The price is $189
Sep 28 - Sep 29
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$164 nightly
The price is $183
Oct 4 - Oct 5
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
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

Holiday Inn Express & Suites Sturbridge by IHG

Holiday Inn Express & Suites Sturbridge by IHG

10/10 Excellent
"I recommend this hotel. Very quiet and clean. Breakfast was really good, especially the coffee machine! The only complaint is the HVAC registers sound like a jet taking off, but there is an off switch! Staff was very good and there is plenty of parking."
Clint 1-night trip
Posted 5 hours ago
Holiday Inn Express & Suites Sturbridge by IHG

Find out more about South Woodstock

Everything you need to know about South Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Woodstock vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Woodstock vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Woodstock. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $128 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Woodstock rentals

At Expedia, we put the best South Woodstock vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Woodstock vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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 Breezy Picnic Grounds & Waterslides, 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.