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 dining area with a high ceiling, skylights, and a view of the outdoors.

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 AU$910
includes taxes & fees
4 Nov - 5 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 AU$279
includes taxes & fees
26 Oct - 27 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 AU$270
includes taxes & fees
28 Oct - 29 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 AU$318
includes taxes & fees
4 Nov - 5 Nov
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A room with two wicker chairs and a small round table, a large window, and a red door.

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 AU$270
includes taxes & fees
28 Oct - 29 Oct
SteamPunk Bunk House and Intergalactic Way Station
Surroundings [summer] (1-5 km)

6. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
The price is AU$144
includes taxes & fees
25 Oct - 26 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 AU$393
includes taxes & fees
4 Nov - 5 Nov
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 AU$537
includes taxes & fees
27 Oct - 28 Oct
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 AU$192
includes taxes & fees
24 Oct - 25 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, (22 reviews)
"Gorgeous property and quiet which helped me sleep very well! I will be returning"
United States
Debra
The price is AU$300
includes taxes & fees
26 Oct - 27 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 AU$186
includes taxes & fees
25 Oct - 26 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.
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 AU$368
includes taxes & fees
28 Oct - 29 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 AU$434
includes taxes & fees
29 Oct - 30 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 AU$362
includes taxes & fees
25 Oct - 26 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 AU$447
includes taxes & fees
26 Oct - 27 Oct
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A round metal fire pit with grilling tools and a red chair in the background.

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 AU$304
includes taxes & fees
27 Oct - 28 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 AU$439
includes taxes & fees
28 Oct - 29 Oct
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 AU$698
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 AU$360
includes taxes & fees
25 Oct - 26 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

Inn on Storrs

Inn on Storrs

10/10 Excellent
"Everything was perfect. We are looking forward to our next stay."
Mystik 2-night trip
Posted 1 day ago
Inn on Storrs

Find out more about Woodstock

Everything you need to know about Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Woodstock holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Woodstock holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as AU$166 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday 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 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 Woodstock holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around 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. 

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.