Woodstock Vacation Rentals

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Woodstock vacation rentals

Fridge, microwave, oven, stovetop
Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (21)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
United States
Savanna
The price is ￥38,595
￥73,975 total
includes taxes & fees
Dec 27 - Dec 28
Stunning Lakefront Escape! Book Your Dream Getaway!
Exterior
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (79)
"Lovely stay on the lake, we enjoyed the location and the kayaks on the lake. "
United States
Lucy H.
The price is ￥42,884
￥77,347 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Private kitchen
Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose
Palmer
9.4 out of 10, Exceptional, (10)
"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"
United States
Edward L.
The price is ￥23,391
￥51,426 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Trainmaster's Inn - Caboose
Interior
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (34)
"We were in town for a family event and the cottage was a perfect choice!Very comfortable, well appointed and just steps from the lake!I'll definitely book again next time I'm in town!"
United States
George J.
The price is ￥19,181
￥44,825 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Property grounds
Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (29)
"My husband and I were exploring a number of birding hotspots in the quiet corner and decided to try the treehouse. We woke to the dawn bird chorus (without any ambient road noise). Just dreamy!"
United States
Jennifer H.
The price is ￥18,401
￥43,461 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Treehouse - Countryside - Farm Animals - Fire Pit
Interior
Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3)
"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 ￥25,964
￥41,087 total
includes taxes & fees
Dec 29 - Dec 30
Spacious, unique barn with beautiful views.
Property grounds
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

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, (48)
"Very nice place to get away and enjoy the lake! Host responded very quickly and was very helpful! Would book again. "
United States
Rachel G.
The price is ￥19,960
￥45,877 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Dining
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.4 out of 10, Exceptional, (39)
"Pet and family, friendly"
United States
Mary-Kate G
The price is ￥18,713
￥43,819 total
includes taxes & fees
Dec 28 - Dec 29
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Property grounds
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

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, (30)
"Great host- fun property!"
United States
Mary F.
The price is ￥18,245
￥46,985 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior
Charming 2-bedroom apartment in welcoming Putnam

Charming 2-bedroom apartment in welcoming Putnam

Charming 2-bedroom apartment in welcoming Putnam
Putnam
9.4 out of 10, Exceptional, (3)
"Very nice place. Quiet neighborhood and close to town. "
United States
michael C.
The price is ￥12,491
￥26,451 total
includes taxes & fees
Dec 28 - Dec 29
Charming 2-bedroom apartment in welcoming Putnam
Interior
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (12)
"Very nice country stay. "
United States
michael C.
The price is ￥17,309
￥40,957 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Interior
Charming 1-bedroom apartment with AC, WiFi in pleasant Webster

Charming 1-bedroom apartment with AC, WiFi in pleasant Webster

Charming 1-bedroom apartment with AC, WiFi in pleasant Webster
2.0 star property
Webster
10.0 out of 10, Exceptional, (1)
"Perfect quiet place to work and rest"
United States
michael C.
The price is ￥28,069
￥63,751 total
includes taxes & fees
Dec 27 - Dec 28
Charming 1-bedroom apartment with AC, WiFi in pleasant Webster
Exterior
SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (14)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
The price is ￥19,648
￥29,301 total
includes taxes & fees
Jan 1 - Jan 2, 2026
SteamPunk Bunk House and Intergalactic Way Station
Interior
Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails

Zen Inspired Retreat with Private Forest Trails
Uxbridge
10.0 out of 10, Exceptional, (14)
"Very comfortable and relaxing on the inside with beautiful surroundings and hiking trails right on the property. Exactly what we wanted for a get-away and such close proximity to the zoo where we attended a wedding."
United States
Tammie K.
Zen Inspired Retreat with Private Forest Trails
Exterior
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (25)
"Hosted a bachelorette trip at this property and it was fantastic. The kayaks and paddle boards provided plenty to do along with a firepit to sit around at night. The house was cozy with plenty of space to sleep 5. Had a great time! "
United States
Renee J.
The price is ￥24,794
￥51,592 total
includes taxes & fees
Dec 29 - Dec 30
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Outdoor dining
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

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

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.4 out of 10, Exceptional, (20)
"We had a nice getaway after a tour of our alma mater, UCONN. This welcoming and very well decorated home gave us a nice place to rest and connect after our busy day."
United States
Andrea F.
The price is ￥21,988
￥48,053 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Exterior
The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (30)
"We had a very nice stay while there."
United States
Ann R.
The price is ￥13,895
￥28,079 total
includes taxes & fees
Jan 25 - Jan 26, 2026
The Carriage House at Chaprae Hall
Interior
New renovation cozy house in Worcester

New renovation cozy house in Worcester

New renovation cozy house in Worcester
Worcester
9.8 out of 10, Exceptional, (17)
"A very lovely stay , calm and quiet "
United States
Alex R.
The price is ￥43,663
￥86,203 total
includes taxes & fees
Jan 23 - Jan 24, 2026
New renovation cozy house in Worcester
Terrace/patio
Apartment in town center #1

Apartment in town center #1

Apartment in town center #1
West Brookfield
8.8 out of 10, Excellent, (26)
"Clean place and was well suited for what we needed"
United States
Chris
The price is ￥12,475
￥46,857 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Apartment in town center #1
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

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent
"We loved being able to have our dog with us - for a very reasonable price. The room was comfortable and coffee and pastries in the morning were fantastic."
nancy 1-night trip
Posted 1 day ago
Publick House Historic Inn and Country Motor Lodge

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 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 Woodstock Golf Course 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.