Woodstock Vacation Rentals

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 9 - Nov 10
Tomorrow
Nov 10 - Nov 11
Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23

Vacation Rentals in Woodstock

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Woodstock
9.8 out of 10, Exceptional, (74)
"We booked this for our friends to stay here while attending our wedding. The place was gorgeous, immaculate, and gave them plenty to do (including kayaking!) while we got ready for the wedding and took photos!"
United States
Maggie Ata W.
The price is ￥40,081
￥75,819 total
includes taxes & fees
Nov 10 - Nov 11
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Fridge, microwave, oven, stovetop
Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!

Woodstock
10.0 out of 10, Exceptional, (20)
"We absolutely loved our stay it was everything I wanted and more. We plan on staying again."
United States
Melissa c.
The price is ￥36,176
￥70,714 total
includes taxes & fees
Nov 10 - Nov 11
Stunning Lakefront Escape! Book Your Dream Getaway!
Smart TV
Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn

Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn

Woodstock
10.0 out of 10, Exceptional, (10)
"Adorable and comfortable property! Highly recommend!"
United States
Lisa M.
Charming country studio apartment in idyllic Woodstock - Woodstock Red Barn
Microwave, stovetop, dishwasher
Poolside Cottage at Woodstock Estates

Poolside Cottage at Woodstock Estates

2.0 star property
Woodstock
Poolside Cottage at Woodstock Estates
Fridge, microwave, oven, stovetop
Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms

Worcester
10.0 out of 10, Exceptional, (4)
"Excellent place to stay, plenty of room and spotless clean"
United States
Ellen y.
The price is ￥42,191
￥78,842 total
includes taxes & fees
Nov 11 - Nov 12
Spacious 4-bedroom with four and half bathrooms
Exterior
The Tree House at Underhill Hollow

The Tree House at Underhill Hollow

Thompson
9.4 out of 10, Exceptional, (33)
"We enjoyed Underhill Hollow, beautiful spot with whimsy & hospitality."
United States
amy m.
The price is ￥16,569
￥26,534 total
includes taxes & fees
Nov 10 - Nov 11
The Tree House at Underhill Hollow
Property grounds
Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit

Willington
9.4 out of 10, Exceptional, (28)
"Great place for a get away!"
United States
Reeshemah N.
The price is ￥15,956
￥39,828 total
includes taxes & fees
Nov 11 - Nov 12
Treehouse - Countryside - Farm Animals - Fire Pit
Exterior
Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow

North Grosvenordale
9.6 out of 10, Exceptional, (20)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
The price is ￥15,189
￥24,064 total
includes taxes & fees
Nov 11 - Nov 12
Wizard's Roost at Underhill Hollow
Dining
Amazing lake house with everything you need!

Amazing lake house with everything you need!

Ashford
9.8 out of 10, Exceptional, (21)
"Great time, lovely location, easy to access and beautiful lake!"
United States
Sam L.
Amazing lake house with everything you need!
Property grounds
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, (28)
"I couldn't believe how prepared the house was in every way. I was very pleased with all the supplies and amenities available. The sun sets over the water hope to be back there again.!!"
United States
Paul B.
The price is ￥17,950
￥47,146 total
includes taxes & fees
Nov 13 - Nov 14
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior
Dove Cabin up in the Trees

Dove Cabin up in the Trees

Holland
9.8 out of 10, Exceptional, (27)
"Great little getaway - Owners are very friendly and accommodating "
United States
Sharon S.
The price is ￥26,925
￥39,487 total
includes taxes & fees
Nov 10 - Nov 11
Dove Cabin up in the Trees
Interior
Bungalow 19 by the lake in Brimfield

Bungalow 19 by the lake in Brimfield

2.0 star property
Brimfield
10.0 out of 10, Exceptional, (1)
"This bungalow was darling. The space was cozy and welcoming. The furniture was comfortable and the throw blankets were so soft. The parking was close to the home, with just a few steps down to the door. I did go up to both lofts, but access was very steep/narrow. It looks cool, but wasn’t particulary useful. Both bedrooms are easily accessible on the ground floor, which I appreciated. The drive up to the bungalow is more of a dirt/gravel road and is a little bumpy, but perfectly...
United States
Jennifer K.
Bungalow 19 by the lake in Brimfield
Property grounds
The Bungalow at Eagleville Lake Under 3 miles to UCONN!

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

Coventry
10.0 out of 10, Exceptional, (70)
"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."
United States
RICHARD P.
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Exterior
Relaxing, Holiday Retreat, Pool, fireplace

Relaxing, Holiday Retreat, Pool, fireplace

Brimfield
10.0 out of 10, Exceptional, (32)
"We stayed at Abigail’s nest a couple weekends ago for a lowkey bachelorette weekend by the pool and Kim and her house were more amazing that we could’ve imagined. The house was absolutely gorgeous and clean and the yard and pool were as well. We relaxed by the pool and had an absolute blast celebrating our bride! We are so grateful to have found this gem! Kim was great and communicative the entire time and we are all grateful for a fantastic weekend. Thanks again Kim!"
United States
Casey G.
Relaxing, Holiday Retreat, Pool, fireplace
Private kitchen
Trainmaster's Inn - Caboose

Trainmaster's Inn - Caboose

Palmer
9.6 out of 10, Exceptional, (8)
"This place is a unique stay, that's for sure! If you are looking for an unforgettable experience, you should come. If you love trains, you should come. However, if you are not that fond of tight spaces or old-fashioned style and your traveling companions are looking for luxury and privacy, you might want to look elsewhere. The bathroom is a big tight (it's a caboose bathroom). But the location is really fun. And the owners are very accommodating! "
United States
Lisa B.
The price is ￥23,013
￥50,759 total
includes taxes & fees
Nov 10 - Nov 11
Trainmaster's Inn - Caboose
Fridge, microwave, oven, stovetop
Impressive Unique Waterfront Pool Resort Country Estate

Impressive Unique Waterfront Pool Resort Country Estate

Southbridge
9.8 out of 10, Exceptional, (56)
"It was wonderful house and property hopefully we will definitely come again. "
United States
Sonam T.
Impressive Unique Waterfront Pool Resort Country Estate
Exterior
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!

West Brookfield
10.0 out of 10, Exceptional, (14)
"Loved the lake house! Would stay again."
United States
Kimberly M.
The price is ￥41,388
￥87,018 total
includes taxes & fees
Nov 13 - Nov 14
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Property grounds
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore

Spencer
10.0 out of 10, Exceptional, (199)
"Water front was a perfectly serene escape. House was cute and had everything we needed for a quiet getaway. Would absolutely stay here again. "
United States
Rich L.
Convenient, clean and cozy 3 bedroom, 2 bath overlooking idyllic lake whittemore
Exterior
Charming 2-bedroom apartment in welcoming Putnam

Charming 2-bedroom apartment in welcoming Putnam

Putnam
9.0 out of 10, Wonderful, (2)
"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 ￥13,255
￥27,133 total
includes taxes & fees
Nov 13 - Nov 14
Charming 2-bedroom apartment in welcoming Putnam
Fridge, microwave, oven, stovetop
Webster Lake - One Home -Two Apartments

Webster Lake - One Home -Two Apartments

Webster
10.0 out of 10, Exceptional, (17)
"Loved our stay here! The place was so cute and had everything we needed for a fun weekend. The game room was so cool and made for some fun evenings. Alison and Denys were so quick with responses for any questions we had. Definitely would recommend staying here. "
United States
Angela K.
Webster Lake - One Home -Two Apartments
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Excellent service.. clean"
phalander 1-night trip
Posted 3 days ago
Wellsworth Hotel

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!: This highly rated vacation home rental in Woodstock 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. Our travelers also rate Stunning Lakefront Escape! Book Your Dream Getaway! as a favorite home for rent in Woodstock.

How many vacation rentals are there in Woodstock?

Expedia has 8 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 Woodstock Golf Course and Roseland Cottage.

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.