Woodstock Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Woodstock

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!

9.8 out of 10, Exceptional, (73)
"We enjoyed our stay, especially sitting on the deck and listening to the birds. We would definitely love to return again sometime."
The price is ￥59,044
￥98,271 total
includes taxes & fees
Oct 20 - Oct 21
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Stunning Lakefront Escape! Book Your Dream Getaway!
Fridge, microwave, oven, stovetop

Stunning Lakefront Escape! Book Your Dream Getaway!

10.0 out of 10, Exceptional, (18)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
The price is ￥47,991
￥84,991 total
includes taxes & fees
Sep 29 - Sep 30
Stunning Lakefront Escape! Book Your Dream Getaway!
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Property grounds

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

9.8 out of 10, Exceptional, (25)
"This prperty was GREAT! Clean, and very accomadating. Had everything you would need staying there. Didn't get to use the lake but sitting on the deck was relaxing. Will book again. 10 Stars!! Thank You!"
The price is ￥7,307
￥32,870 total
includes taxes & fees
Sep 29 - Sep 30
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Brimfield Waterfront cottage
Property grounds

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (9)
"Property is in excellent condition, just the right amount of space for us. "
Brimfield Waterfront cottage
The Tree House at Underhill Hollow
Exterior

The Tree House at Underhill Hollow

9.4 out of 10, Exceptional, (32)
"My 10 year old loved this stay! Meeting the goats and sheep was fun and it was located in a nice area. Would love to visit again!"
The price is ￥15,942
￥25,529 total
includes taxes & fees
Sep 25 - Sep 26
The Tree House at Underhill Hollow
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
Property grounds

Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!

10.0 out of 10, Exceptional, (132)
"It was our 4 lake vacation there. We absolutely love it and our dog Charlie enjoys the beautiful yard and and a swim in a little bay at this property."
Waterfront Home with Stunning Views .. Dog friendly , and great fishing !!!
Amazing lake house with everything you need!
Dining

Amazing lake house with everything you need!

9.8 out of 10, Exceptional, (17)
"Great time, lovely location, easy to access and beautiful lake!"
Amazing lake house with everything you need!
Dove Cabin up in the Trees
Exterior

Dove Cabin up in the Trees

9.8 out of 10, Exceptional, (23)
"This is the sweetest property to stay in when visiting Brimfield market. I highly suggest any of the cabins on the property "
The price is ￥25,906
￥37,992 total
includes taxes & fees
Sep 28 - Sep 29
Dove Cabin up in the Trees
Treehouse - Countryside - Farm Animals - Fire Pit
Property grounds

Treehouse - Countryside - Farm Animals - Fire Pit

9.4 out of 10, Exceptional, (27)
"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!"
The price is ￥20,384
￥44,837 total
includes taxes & fees
Sep 25 - Sep 26
Treehouse - Countryside - Farm Animals - Fire Pit
Spacious 2 Bedroom 1 Bath apt
Dining

Spacious 2 Bedroom 1 Bath apt

10.0 out of 10, Exceptional, (1)
"Great host and excellent apartment "
The price is ￥19,994
￥47,562 total
includes taxes & fees
Oct 9 - Oct 10
Spacious 2 Bedroom 1 Bath apt
Wizard's Roost at Underhill Hollow
Exterior

Wizard's Roost at Underhill Hollow

9.6 out of 10, Exceptional, (17)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
The price is ￥14,613
￥23,152 total
includes taxes & fees
Sep 25 - Sep 26
Wizard's Roost at Underhill Hollow
Spacious 4-bedroom with four and half bathrooms
Fridge, microwave, oven, stovetop

Spacious 4-bedroom with four and half bathrooms

10.0 out of 10, Exceptional, (4)
"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."
The price is ￥40,593
￥74,165 total
includes taxes & fees
Sep 25 - Sep 26
Spacious 4-bedroom with four and half bathrooms
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Outdoor dining

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

9.8 out of 10, Exceptional, (114)
"The weather didn’t cooperate enough for us to enjoy the water, but it was lovely to look at"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Interior

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

9.8 out of 10, Exceptional, (32)
"Comfortable and as described "
The price is ￥20,679
￥45,177 total
includes taxes & fees
Sep 25 - Sep 26
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Exterior

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

9.0 out of 10, Wonderful, (21)
"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! "
The price is ￥18,304
￥42,136 total
includes taxes & fees
Sep 29 - Sep 30
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
Dining

Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

9.8 out of 10, Exceptional, (57)
"Came into town for a wedding and the house was perfectly located and maintained"
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest
Luxury Home, Pool, fireplace
Exterior

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (29)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
Luxury Home, Pool, fireplace
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Property grounds

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

10.0 out of 10, Exceptional, (67)
"Great place to stay if you're looking for a quiet get away. The house was very clean, and the host had everything needed to make the stay as comfortable as possible. Very quiet street. I would recommend this property to anyone looking for nice relaxing vacation."
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
SteamPunk Bunk House and Intergalactic Way Station
Exterior

SteamPunk Bunk House and Intergalactic Way Station

10.0 out of 10, Exceptional, (11)
"This was a charming little apartment with a unique steam punk alien theme. If you have a playful mindset, I highly recommend staying at this location. I couldn’t have been more overjoyed with my stay."
The price is ￥15,942
￥24,681 total
includes taxes & fees
Sep 28 - Sep 29
SteamPunk Bunk House and Intergalactic Way Station
Charming 4-bedroom house with WiFi and AC in wonderful Killingly
Iron/ironing board, WiFi, bed sheets

Charming 4-bedroom house with WiFi and AC in wonderful Killingly

The price is ￥46,172
￥114,585 total
includes taxes & fees
Oct 1 - Oct 2
Charming 4-bedroom house with WiFi and AC in wonderful Killingly
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Woodstock Hotel Reviews

La Quinta Inn by Wyndham Auburn Worcester

La Quinta Inn by Wyndham Auburn Worcester

10/10 Excellent
"Good clean place "
Christopher 1-night trip
Posted 2 days ago
La Quinta Inn by Wyndham Auburn Worcester

Find out more about Woodstock

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 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 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.