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

Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Woodstock vacation rentals

Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (26 reviews)
"Great experience. Thank you "
United States
edmund d.
$655 nightly
The price is $741
Jul 16 - Jul 17
Total with taxes and fees
Stunning Lakefront Escape! Book Your Dream Getaway!
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (86 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$680 nightly
The price is $770
Jul 19 - Jul 20
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Coventry Lake
9.8 out of 10, Exceptional, (43 reviews)
"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.
$330 nightly
The price is $374
Jul 16 - Jul 17
Total with taxes and fees
Lakefront - King - W&D - PetsOK - Kayaks - SUPs
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (31 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
$244 nightly
The price is $257
Jul 16 - Jul 17
Total with taxes and fees
Dove Cabin up in the Trees
Terrace/patio

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, (45 reviews)
"Very nice area."
United States
maureen p.
$313 nightly
The price is $354
Jul 19 - Jul 20
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Interior

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.
$171 nightly
The price is $194
Jul 20 - Jul 21
Total with taxes and fees
The Tree House at Underhill Hollow
Exterior detail

Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (1 review)
"We were up in Pomfret for a wedding in the area. Perfect location for us; walkable to a local cafe (Vanilla Bean) for breakfast. The place sits on a large piece of property complete with pond; beautiful setting, very peaceful. Plenty of space for parking; water pressure was great for showers and appreciate the travel size lotions, shampoo, etc ! Overall a great experience. Would highly recommend, especially for parents of students who attend The Pomfret School (boarding). Perfect location...
United States
Stephanie K.
$277 nightly
The price is $314
Jul 16 - Jul 17
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Private kitchen

Clean & Cozy Private room - 3 floor_R 1

Clean & Cozy Private room - 3 floor_R 1
Union HIll
$100 nightly
The price is $115
Jul 20 - Jul 21
Total with taxes and fees
Clean & Cozy Private room - 3 floor_R 1
TV, fireplace

Sleeps 15 • Pool • Retreat

Sleeps 15 • Pool • Retreat
Brimfield
10.0 out of 10, Exceptional, (36 reviews)
"We visited in December, so the pool was closed, but looked inviting even in the snow. The home was so warm and cozy and spacious. We loved our stay."
United States
Gina O.
$1,460 nightly
The price is $1,630
Jul 19 - Jul 20
Total with taxes and fees
Sleeps 15 • Pool • Retreat
Coffee/tea maker, fridge, microwave, oven

Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms
Worcester
10.0 out of 10, Exceptional, (12 reviews)
"Perfect location"
United States
Harmony F.
$446 nightly
The price is $510
Jul 16 - Jul 17
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
TV

Large 3BD 1st Floor Apartment Minutes from 290

Large 3BD 1st Floor Apartment Minutes from 290
Franklin Plantation
10.0 out of 10, Exceptional, (3 reviews)
"It was a great place for my family and i"
United States
Taisha M.
$277 nightly
The price is $317
Jul 16 - Jul 17
Total with taxes and fees
Large 3BD 1st Floor Apartment Minutes from 290
Exterior

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

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (36 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
$394 nightly
The price is $446
Jul 19 - Jul 20
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Property grounds

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, (52 reviews)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
$312 nightly
The price is $353
Aug 4 - Aug 5
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Beach nearby

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

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.2 out of 10, Wonderful, (45 reviews)
"The property was clean and accommodating."
United States
Ann Marie T.
$337 nightly
The price is $382
Jul 27 - Jul 28
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
10.0 out of 10, Exceptional, (3 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.
$234 nightly
The price is $264
Jul 20 - Jul 21
Total with taxes and fees
Spacious, unique barn with beautiful views.
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (23 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.
$166 nightly
The price is $188
Jul 19 - Jul 20
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Outdoor dining

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)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
$348 nightly
The price is $394
Jul 19 - Jul 20
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Smart TV

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2

Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Worcester
10.0 out of 10, Exceptional, (5 reviews)
"Clean, perfect, had everything we needed for a quick stay "
United States
Sierra M.
$458 nightly
The price is $524
Jul 17 - Jul 18
Total with taxes and fees
Newly Renovated 4BR Worcester Home • Pet-Friendly • Near I-290 & Park 16-2
Dining

The Grand Beam Residence • Luxury 3BR + King Suite

The Grand Beam Residence • Luxury 3BR + King Suite
Worcester
10.0 out of 10, Exceptional, (1 review)
"Terrific place. Even better than the photos. Plenty of space. Very nice property manager. "
United States
David P.
$395 nightly
The price is $452
Jul 17 - Jul 18
Total with taxes and fees
The Grand Beam Residence • Luxury 3BR + King Suite
Smart TV, books

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern

Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
Coventry
9.8 out of 10, Exceptional, (7 reviews)
$263 nightly
The price is $298
Jul 22 - Jul 23
Total with taxes and fees
Walk to Everything! Lake, Park, Dining, Antiques & The Famous Bidwell Tavern
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

8/10 Good
"The restaurant served a rotten food fish to me. The floor was unleveled. A men's chest was not affixed to the wall and whith an unleveled floor it can fall and hurt a child on room 5."
Leonel 2-night trip
Posted 6 hours ago
Publick House Historic Inn and Country Motor Lodge

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 $108 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!: 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 7 vacation rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Muddy Pond and Black Pond 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.