A variety of potted flowers and pumpkins on a wooden table in an outdoor setting.

Woodstock Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Woodstock vacation rentals

A dining area with a high ceiling, skylights, and a view of the outdoors.

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

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (93 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$563 nightly
The price is $638
Nov 1 - Nov 2
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

2. The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (44 reviews)
$171 nightly
The price is $194
Oct 15 - Oct 16
Total with taxes and fees
The Tree House at Underhill Hollow
A red building with a colorful mural on the front, a covered porch, and a stone foundation.

3. Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (26 reviews)
"Great stay!!"
United States
Elizabeth G.
$166 nightly
The price is $188
Oct 18 - Oct 19
Total with taxes and fees
Wizard's Roost at Underhill Hollow
A two-story house with a front porch, stone steps, and a driveway.

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

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
9.0 out of 10, Wonderful, (8 reviews)
"Very convenient 2BD for a two night stay. Note that parking is on the street."
United States
Dan M.
$191 nightly
The price is $216
Oct 19 - Oct 20
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
A rustic building with a brick exterior and a red roof, situated next to a pond with tall reeds and a tree with autumn-colored leaves.

5. SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (18 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$166 nightly
The price is $188
Oct 15 - Oct 16
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Bedroom

6. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Putnam
$88 nightly
The price is $101
Oct 18 - Oct 19
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A house with a white porch, a black door, and a window with a white frame.

7. Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
9.0 out of 10, Wonderful, (4 reviews)
"Great spot, clean and cozy."
United States
Bud n' Mary's Marina B.
$277 nightly
The price is $314
Oct 15 - Oct 16
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
A bedroom with a wooden bed, large windows, and a view of greenery outside.

8. Rustic Farmette Studio with Hot Tub & Pool

Rustic Farmette Studio with Hot Tub & Pool
Thompson
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful and quiet location"
United States
Lynn J.
$339 nightly
The price is $384
Oct 16 - Oct 17
Total with taxes and fees
Rustic Farmette Studio with Hot Tub & Pool
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$117 nightly
The price is $131
Oct 15 - Oct 16
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
A room with a blue wall, a mirror, a table with chairs, potted plants, and a Christmas tree.

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

Modern 1-bedroom apartment in peaceful Sturbridge with AC
Sturbridge
6.0 out of 10, (3 reviews)
"Clean place short drive to all Sturbridge attractions."
United States
Lynn M. T.
$115 nightly
The price is $128
Oct 15 - Oct 16
Total with taxes and fees
Modern 1-bedroom apartment in peaceful Sturbridge with AC
A group of people seated around a fire pit in a garden with a gazebo and trees in the background.

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

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.6 out of 10, Exceptional, (20 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
$200 nightly
The price is $227
Oct 21 - Oct 22
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
A modern interior with a kitchen, dining area, and living space.

12. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
10.0 out of 10, Exceptional, (1 review)
"Edgar was very responsive and easy to work with. The unit was very clean and well kept. I would definitely stay there again."
United States
debra l.
6 Beds Home w/Game Room Perfect for Groups
A window with a view of a grassy field and trees.

13. Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.8 out of 10, Exceptional, (7 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.
$258 nightly
The price is $294
Oct 16 - Oct 17
Total with taxes and fees
Spacious, unique barn with beautiful views.
A wooden cabin with a glass upper floor, surrounded by a forest.

14. Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (38 reviews)
"Wonderful cabin wishing it was a waterfront"
United States
Magdalena W.
$244 nightly
The price is $257
Oct 15 - Oct 16
Total with taxes and fees
Dove Cabin up in the Trees
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

15. Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
A wooden cabin with a balcony and stairs, surrounded by trees.

16. Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (37 reviews)
$262 nightly
The price is $297
Oct 15 - Oct 16
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
A wooden deck with outdoor furniture, overlooking a lake with boats and houses in the background.

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, (49 reviews)
"Better than pictured. Beautiful lake and decks! Super comfortable living room furniture. Near great local restaurants."
United States
Julianne
$282 nightly
The price is $320
Oct 19 - Oct 20
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
A wooden bench and a small wooden bridge in a natural setting with greenery and a stream.

18. 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, (10 reviews)
$206 nightly
The price is $230
Nov 3 - Nov 4
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

19. Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (3 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
$285 nightly
The price is $318
Oct 26 - Oct 27
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
A cozy outdoor seating area with a fire feature, two drinks, and hanging plants.

20. Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!

Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
Webster
10.0 out of 10, Exceptional, (3 reviews)
"We loved the space, it accommodated our larger group and had all the amenities we needed. We only stayed 1 night but would have loved to stay longer! The porch area was very nice to sit out on at night."
United States
Kyle C.
Family-friendly 5-Bedroom Webster Home w/ Cozy Balcony - Perfect for Families!
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

Graduate by Hilton Storrs

Graduate by Hilton Storrs

10/10 Excellent
"This was a great hotel for our UConn visit. The furnishings and decor were very fun and UConn themed. The staff were very nice. We would definitely stay there again."
Melissa 1-night trip
Posted 3 hours ago
Graduate by Hilton Storrs

Find out more about Woodstock

Everything you need to know about Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodstock vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $115 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodstock vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.