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Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Woodstock vacation rentals

Terrace/patio

1. Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (27 reviews)
"We loved the house and the grounds looking over the lake. The house was very clean and had everything we needed. The yard, front and back were really lovely. The backyard overlooked Quasset Lake. We were fortunate to enjoy pleasant weather. The beds were comfortable. The living room and kitchen overlooked the lake with a large deck off the area. There is shade available over the deck if the sun gets too hot. We were there only for the weekend, but had a fabulous time."
United States
Gayle B.
The price is ￥71,591
￥118,244 total
includes taxes & fees
Aug 30 - Aug 31
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (88 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
The price is ￥79,475
￥128,392 total
includes taxes & fees
Sep 2 - Sep 3
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Iron/ironing board, WiFi, bed sheets

3. 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
The price is ￥27,180
￥38,642 total
includes taxes & fees
Aug 30 - Aug 31
Cozy 2-bedroom cabin in welcoming Holland with AC comfort at Mishnoah Retreat
Interior

4. Game Room + Bar Lounge, 35 Min to Boston

Game Room + Bar Lounge, 35 Min to Boston
Worcester
The price is ￥32,473
￥42,625 total
includes taxes & fees
Aug 31 - Sep 1
Game Room + Bar Lounge, 35 Min to Boston
Smart TV

5. 1.8 miles 5 minutes drive to UConn.Spacious 4-bedroom house.Quiet neighborhood!

1.8 miles 5 minutes drive to UConn.Spacious 4-bedroom house.Quiet neighborhood!
Willington
The price is ￥40,520
￥52,485 total
includes taxes & fees
Sep 14 - Sep 15
1.8 miles 5 minutes drive to UConn.Spacious 4-bedroom house.Quiet neighborhood!
Interior

6. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (40 reviews)
"Great space, lots of fun."
United States
Douglas C.
The price is ￥20,028
￥31,099 total
includes taxes & fees
Sep 1 - Sep 2
The Tree House at Underhill Hollow
Exterior

7. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (24 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 ￥20,028
￥29,867 total
includes taxes & fees
Aug 30 - Aug 31
Wizard's Roost at Underhill Hollow
Property grounds

8. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is ￥20,028
￥29,867 total
includes taxes & fees
Aug 30 - Aug 31
SteamPunk Bunk House and Intergalactic Way Station
Exterior

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (6 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 ￥18,597
￥34,341 total
includes taxes & fees
Sep 23 - Sep 24
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior detail

10. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (2 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 ￥38,943
￥50,348 total
includes taxes & fees
Sep 22 - Sep 23
Cozy 1-bedroom cottage in serene Pomfret.
Exterior

11. The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
The price is ￥21,477
￥38,142 total
includes taxes & fees
Sep 20 - Sep 21
The Carriage House at Chaprae Hall
Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
The price is ￥9,545
￥22,923 total
includes taxes & fees
Aug 26 - Aug 27
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Exterior

13. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
"Loved my "staycation" at the Tree house. I just needed a couple of days to relax. Carmen and Joe are very friendly. Loved the location, the scenery and the animals. Great place to unwind. Would love to go back some time, maybe in the fall, I bet it's beautiful."
United States
mythra 7.
The price is ￥17,898
￥43,811 total
includes taxes & fees
Aug 30 - Aug 31
Treehouse - Countryside - Farm Animals - Fire Pit
Interior

14. 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.
The price is ￥26,488
￥42,553 total
includes taxes & fees
Aug 30 - Aug 31
Spacious, unique barn with beautiful views.
Exterior

15. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (35 reviews)
"The owner was pleasant and accommodating "
United States
Maryann
The price is ￥27,896
￥41,415 total
includes taxes & fees
Sep 3 - Sep 4
Dove Cabin up in the Trees
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (39 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.
The price is ￥25,709
￥53,906 total
includes taxes & fees
Aug 29 - Aug 30
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Terrace/patio

17. 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, (48 reviews)
"We had a great time swimming and kayaking. The house was spotless. Lake front with great parking."
United States
Christy
The price is ￥20,682
￥52,540 total
includes taxes & fees
Sep 11 - Sep 12
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (17 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 ￥11,168
￥34,957 total
includes taxes & fees
Sep 3 - Sep 4
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (23 reviews)
"Place was really nice and in a location that made it easy to get back and forth to UCONN. "
United States
Jason C.
The price is ￥25,454
￥53,454 total
includes taxes & fees
Aug 26 - Aug 27
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
TV

20. 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
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

La Quinta Inn by Wyndham Auburn Worcester

La Quinta Inn by Wyndham Auburn Worcester

10/10 Excellent
"Awesome"
David 1-night trip
Posted 1 hour ago
La Quinta Inn by Wyndham Auburn Worcester

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
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  • 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 vacation rental in Woodstock?

Yes, we give you a choice of vacation rentals close to well known attractions in Woodstock, or you can go with a more remote option if you'd like a relaxing place to 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 vacation rentals in Woodstock?

Secluded 2-Acre Lakefront Home! Book Your Getaway!: Visitors give good reviews to this Woodstock vacation home rental, which is located on a lake and has a patio, a selection of games, and a barbecue grill 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 you can cook with friends or family.

How many vacation rentals are there in Woodstock?

Expedia has 7 vacation rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Black Pond and Muddy Pond are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Roseland Cottage and Taylor Brooke Winery.

What are vacation rentals like in Woodstock?

Vacation rentals are private accommodations you can reserve for a couple days or more in Woodstock. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for small groups.