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

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)
"Great experience. Thank you "
United States
edmund d.
$657 nightly
The price is $743
Aug 11 - Aug 12
Total with taxes and fees
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.
$714 nightly
The price is $808
Sep 1 - Sep 2
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Exterior detail

3. 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.
$277 nightly
The price is $314
Aug 12 - Aug 13
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Interior

4. 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.
$173 nightly
The price is $196
Aug 11 - Aug 12
Total with taxes and fees
The Tree House at Underhill Hollow
Exterior

5. 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.
$167 nightly
The price is $189
Aug 13 - Aug 14
Total with taxes and fees
Wizard's Roost at Underhill Hollow
House (5 Bedrooms) | Interior

6. Quintessential New England Home w/ Patio & Grill!

Quintessential New England Home w/ Patio & Grill!
3.0 star property
Putnam
Quintessential New England Home w/ Patio & Grill!
Exterior detail

7. Quintessential New England Home w/ Patio & Grill!

Quintessential New England Home w/ Patio & Grill!
Putnam
10.0 out of 10, Exceptional, (8 reviews)
"A perfect place to bring our family together to celebrate our parents’ 50th anniversary! The house had everything we needed, was beautifully decorated and thoughtfully furnished, and felt warm and welcoming from the moment we arrived. A truly special stay."
United States
Laurie and Dan C.
Quintessential New England Home w/ Patio & Grill!
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.
$167 nightly
The price is $189
Aug 17 - Aug 18
Total with taxes and fees
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.
$201 nightly
The price is $227
Sep 9 - Sep 10
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Exterior

10. 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.
$247 nightly
The price is $261
Aug 11 - Aug 12
Total with taxes and fees
Dove Cabin up in the Trees
Exterior

11. The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
The Carriage House at Chaprae Hall
Interior

12. 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.
$237 nightly
The price is $267
Aug 13 - Aug 14
Total with taxes and fees
Spacious, unique barn with beautiful views.
Exterior

13. 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)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
$354 nightly
The price is $400
Sep 1 - Sep 2
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Outdoor dining

14. 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.
$331 nightly
The price is $374
Aug 19 - Aug 20
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
TV

15. 6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
$592 nightly
The price is $702
Aug 11 - Aug 12
Total with taxes and fees
6 Beds Home w/Game Room Perfect for Groups
Coffee/tea maker, fridge, microwave, oven

16. Mohegan Sun Getaway Large Group Retreat

Mohegan Sun Getaway Large Group Retreat
Killingly
7.4 out of 10, Good, (3 reviews)
$589 nightly
The price is $699
Aug 11 - Aug 12
Total with taxes and fees
Mohegan Sun Getaway Large Group Retreat
Terrace/patio

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

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.8 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
$313 nightly
The price is $354
Sep 1 - Sep 2
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Interior

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

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$124 nightly
The price is $139
Aug 11 - Aug 12
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
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.
$177 nightly
The price is $197
Aug 11 - Aug 12
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Property grounds

20. Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!

Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
Sturbridge
10.0 out of 10, Exceptional, (94 reviews)
"Amazing place to gather and relax. "
United States
Evan M.
Direct waterfront Lake House, stunning views Sleeps 8 on a private PENINSULA!
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

Wellsworth Hotel

Wellsworth Hotel

8/10 Good
"Great stay! Impressive ambiance. Spacious rooms. Amenities galore."
Cynthia 1-night trip
Posted less than an hour ago
Wellsworth Hotel

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 $106 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.