A variety of potted flowers and pumpkins on a wooden table in an outdoor setting.

Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Woodstock holiday rentals

A wooden staircase leading to a room with a radiator and a potted plant.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (94 reviews)
"Beautiful lake house. The dock with the kayaks and paddle boat made it so much fun for the kids. The dock isnt far from the house but there a decent hill down to it. Totally manageable for most people though. The open house concept kitchen area made it great for everyone to be together."
United States
Amanda S.
The price is HK$2,943
HK$5,038 total
includes taxes & fees
2 Nov - 3 Nov
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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, (44 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is HK$989
HK$1,520 total
includes taxes & fees
22 Oct - 23 Oct
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

3. 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 HK$989
HK$1,475 total
includes taxes & fees
21 Oct - 22 Oct
Wizard's Roost at Underhill Hollow
A two-story house with a front porch, stone steps, and a driveway.

4. 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 HK$961
HK$1,713 total
includes taxes & fees
27 Oct - 28 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.

5. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (19 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is HK$989
HK$1,475 total
includes taxes & fees
21 Oct - 22 Oct
SteamPunk Bunk House and Intergalactic Way Station
A building with a number '6' sign, a parking lot, and a clear sky.

6. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
The price is HK$689
HK$793 total
includes taxes & fees
21 Oct - 22 Oct
1 King Bed | Non-Smoking, Micfridge
A house with a white porch, a black door, and a window with a white frame.

7. 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 HK$1,687
HK$2,160 total
includes taxes & fees
25 Oct - 26 Oct
Cozy 1-bedroom cottage in serene Pomfret.
A bedroom with a wooden bed, large windows, and a view of greenery outside.

8. 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 HK$1,727
HK$2,712 total
includes taxes & fees
15 Nov - 16 Nov
Rustic Farmette Studio with Hot Tub & Pool
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
4.0 out of 10, (1 review)
The price is HK$353
HK$999 total
includes taxes & fees
21 Oct - 22 Oct
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (21 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$471
HK$1,601 total
includes taxes & fees
21 Oct - 22 Oct
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.

11. 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 HK$746
HK$1,008 total
includes taxes & fees
21 Oct - 22 Oct
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A modern interior with a kitchen, dining area, and living space.

12. 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 HK$1,424
HK$4,541 total
includes taxes & fees
21 Oct - 22 Oct
6 Beds Home w/Game Room Perfect for Groups
A wooden cabin with a balcony and stairs, surrounded by trees.

13. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"The tree house was amazing! The surroundings are great, flower garden, farm animals, and the hosts were very friendly and gracious. Our kids loved feeding the sheep with Carmen. Highly recommend!"
United States
Esther R.
The price is HK$628
HK$1,781 total
includes taxes & fees
21 Oct - 22 Oct
Treehouse - Countryside - Farm Animals - Fire Pit
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 HK$1,554
HK$2,305 total
includes taxes & fees
23 Oct - 24 Oct
Spacious, unique barn with beautiful views.
A wooden cabin with a glass upper floor, surrounded by a forest.

15. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (38 reviews)
"Wonderful cabin wishing it was a waterfront"
United States
Magdalena W.
The price is HK$1,377
HK$2,020 total
includes taxes & fees
26 Oct - 27 Oct
Dove Cabin up in the Trees
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 HK$934
HK$2,445 total
includes taxes & fees
21 Oct - 22 Oct
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

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, (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 HK$1,455
HK$1,836 total
includes taxes & fees
22 Oct - 23 Oct
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.

18. 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 HK$1,177
HK$2,472 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A hotel with a central building, outdoor seating area, and a covered patio.

19. 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 traveller
The price is HK$1,942
HK$3,932 total
includes taxes & fees
2 Nov - 3 Nov
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
A house with a stone chimney, a fire pit, and two Adirondack chairs in the yard.

20. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (54 reviews)
"Very cute little place to spend a weekend! My friends, partner, and I slept comfortably. The lake itself is very nice (though weather unfortunately prevented us from going out on it with the kayaks) and it is within a short drive to Hartford, UConn, and plenty of things to do. Connecticut is such a lovely state! The purpose of our trip was so that my partner and I could look at apartments in town. We were already excited to move to CT, but after this trip, we became completely confident in how...
United States
Austin R.
The price is HK$804
HK$2,046 total
includes taxes & fees
22 Oct - 23 Oct
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
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 Woodstock Hotel Reviews

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"so much fun in the racquet ball courts. pool and hot tubs. Great wedding venue. nice bar. large rooms. would come again!"
CATHARINE 1-night trip
Posted 8 hours ago
Wellsworth Hotel

Find out more about Woodstock

Search for holiday rentals in Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodstock using one of the methods below:

  • View our selection of featured holiday rentals in Woodstock
  • Use the map to find apartments and other holiday homes in the Woodstock neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodstock while they last

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

Frequently asked questions

Can I find a holiday rental in Woodstock?

Yes, there are holiday rentals close to the most popular sights in Woodstock, or you can select a more secluded option if you're looking for a relaxing stay. Woodstock is known for its festivals and wineries. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best holiday rentals that Woodstock has to offer?

Secluded 2-Acre Lakefront Home! Book Your Getaway!: This highly rated holiday home rental in Woodstock is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Woodstock?

Expedia has 7 holiday rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Black Pond and Woodstock Town Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Roseland Cottage and Woodstock Golf Course.

What are holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for families.