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Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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)
"Welcoming host! Beautiful house with great amenities!"
United States
maria c.
The price is AED 1,836
AED 2,967 total
includes taxes & fees
30 Aug - 31 Aug
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, (87 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 1,836
AED 2,967 total
includes taxes & fees
1 Sep - 2 Sep
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 AED 628
AED 893 total
includes taxes & fees
15 Aug - 16 Aug
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 AED 750
AED 985 total
includes taxes & fees
20 Aug - 21 Aug
Game Room + Bar Lounge, 35 Min to Boston
Exterior detail

5. 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 AED 900
AED 1,163 total
includes taxes & fees
15 Aug - 16 Aug
Cozy 1-bedroom cottage in serene Pomfret.
Interior

6. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
The price is AED 463
AED 711 total
includes taxes & fees
21 Aug - 22 Aug
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 AED 463
AED 694 total
includes taxes & fees
25 Aug - 26 Aug
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, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is AED 463
AED 694 total
includes taxes & fees
17 Aug - 18 Aug
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 AED 559
AED 949 total
includes taxes & fees
24 Aug - 25 Aug
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Outdoor dining

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (22 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 AED 591
AED 1,237 total
includes taxes & fees
17 Aug - 18 Aug
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Interior

11. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (5 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 612
AED 982 total
includes taxes & fees
16 Aug - 17 Aug
Spacious, unique barn with beautiful views.
Exterior

12. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.6 out of 10, Exceptional, (34 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
The price is AED 645
AED 957 total
includes taxes & fees
16 Aug - 17 Aug
Dove Cabin up in the Trees
Exterior

13. 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 AED 386
AED 735 total
includes taxes & fees
26 Aug - 27 Aug
The Carriage House at Chaprae Hall
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (37 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 AED 833
AED 1,546 total
includes taxes & fees
13 Sep - 14 Sep
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Coffee/tea maker, fridge, microwave, oven

15. 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 738
AED 2,620 total
includes taxes & fees
18 Aug - 19 Aug
Mohegan Sun Getaway Large Group Retreat
Terrace/patio

16. Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.8 out of 10, Exceptional, (46 reviews)
"We had a great time swimming and kayaking. The house was spotless. Lake front with great parking."
United States
Christy
The price is AED 477
AED 1,206 total
includes taxes & fees
11 Sep - 12 Sep
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior

17. 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 AED 608
AED 1,258 total
includes taxes & fees
13 Sep - 14 Sep
Treehouse - Countryside - Farm Animals - Fire Pit
Interior

18. Modern 1-bedroom apartment in peaceful Sturbridge with AC

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
8.0 out of 10, Very Good, (1 review)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
The price is AED 217
AED 324 total
includes taxes & fees
15 Aug - 16 Aug
Modern 1-bedroom apartment in peaceful Sturbridge with AC
Property grounds

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, (7 reviews)
"Welcoming, cute."
United States
Trinity M.
The price is AED 578
AED 741 total
includes taxes & fees
18 Aug - 19 Aug
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
TV, fireplace

20. Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (38 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
The price is AED 3,223
AED 5,914 total
includes taxes & fees
31 Aug - 1 Sep
Sleeps 15 • Pool • Retreat
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

Homewood Suites By Hilton Worcester

Homewood Suites By Hilton Worcester

10/10 Excellent
"Great for a 4 night stay with kids. Breakfast was average, pool was clean, room and bed comfortable. We were able to see fireworks from our window one night at the Woosox game!"
Alexandra 4-night trip
Posted 8 hours ago
Homewood Suites By Hilton Worcester

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 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 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.