Woodstock Vacation Rentals

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Oct 25 - Oct 26
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Vacation Rentals in Woodstock

Exterior
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Secluded 2-Acre Lakefront Home! Book Your Getaway!
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.
$436 nightly
The price is $494
Nov 1 - Nov 2
Total with taxes and fees
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!
10.0 out of 10, Exceptional, (19)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
United States
Savanna
$421 nightly
The price is $476
Nov 1 - Nov 2
Total with taxes and fees
Stunning Lakefront Escape! Book Your Dream Getaway!
Microwave, stovetop, dishwasher
Poolside Cottage at Woodstock Estates
Poolside Cottage at Woodstock Estates
2.0 star property
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
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."
United States
Deb H.
$446 nightly
The price is $510
Oct 26 - Oct 27
Total with taxes and fees
Spacious 4-bedroom with four and half bathrooms
Exterior
The Tree House at Underhill Hollow
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!"
United States
Becky B.
$153 nightly
The price is $173
Oct 26 - Oct 27
Total with taxes and fees
The Tree House at Underhill Hollow
Property grounds
Treehouse - Countryside - Farm Animals - Fire Pit
Treehouse - Countryside - Farm Animals - Fire Pit
9.4 out of 10, Exceptional, (27)
"Safe, inviting stay."
United States
Gabe M.
$248 nightly
The price is $281
Oct 30 - Oct 31
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
Dining
Amazing lake house with everything you need!
Amazing lake house with everything you need!
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!
Exterior
Wizard's Roost at Underhill Hollow
Wizard's Roost at Underhill Hollow
9.6 out of 10, Exceptional, (19)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
$139 nightly
The price is $157
Oct 26 - Oct 27
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Property grounds
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
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!"
United States
WILLIAM
$273 nightly
The price is $309
Oct 26 - Oct 27
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Exterior
Dove Cabin up in the Trees
Dove Cabin up in the Trees
9.8 out of 10, Exceptional, (27)
"A sweet, cozy, nostalgic little cabin in the woods. It was the perfect stop over on our road trip to Acadia. Very peaceful, and the screened in porch was wonderful to relax on before bed and during breakfast. "
United States
Maggie G.
$244 nightly
The price is $257
Oct 26 - Oct 27
Total with taxes and fees
Dove Cabin up in the Trees
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
10.0 out of 10, Exceptional, (198)
"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
Spacious Massachusetts Apartment #2
Spacious Massachusetts Apartment #2
9.0 out of 10, Wonderful, (28)
"The apartment was very clean. It’s cozy, but had enough room for my family of 4. The house it’s a classic older New England home. It’s in the downtown part of a small cute town. Overall it was a really good experience!"
United States
Kathleen S.
$269 nightly
The price is $300
Oct 29 - Oct 30
Total with taxes and fees
Spacious Massachusetts Apartment #2
Property grounds
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
10.0 out of 10, Exceptional, (70)
"Very beautiful place. Lovely to catch up with friends."
United States
Marilyn M.
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Exterior
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
9.2 out of 10, Wonderful, (23)
"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! "
United States
Renee J.
$325 nightly
The price is $368
Oct 29 - Oct 30
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
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!
10.0 out of 10, Exceptional, (14)
"The house was beautiful. Very clean, pet friendly, very good communication with owner."
United States
JUNE
Hillside Hideaway: full family home, 250 ft from the lake shore. Dog friendly!
Fridge, microwave, oven, stovetop
Impressive Unique Waterfront Pool Resort Country Estate
Impressive Unique Waterfront Pool Resort Country Estate
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
Dining
Large relaxing house in 25 acres of private woods with lake access.
Large relaxing house in 25 acres of private woods with lake access.
9.6 out of 10, Exceptional, (24)
"Beautiful place and we had a great family weekend"
United States
William M.
Large relaxing house in 25 acres of private woods with lake access.
Outdoor dining
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
9.8 out of 10, Exceptional, (116)
"Great place to stay. Loved the lake. The kids could hang out on the dock and swim all day. Nice quit neighborhood to enjoy family and relax. "
United States
Melissa T.
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!
Exterior
Relaxing, Holiday Retreat, Pool, fireplace
Relaxing, Holiday Retreat, Pool, fireplace
10.0 out of 10, Exceptional, (32)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
United States
Danneel A.
Relaxing, Holiday Retreat, Pool, fireplace
Interior
New renovation cozy house in Worcester
New renovation cozy house in Worcester
2.0 star property
9.8 out of 10, Exceptional, (14)
"A very lovely stay , calm and quiet "
United States
Alex R.
$500 nightly
The price is $572
Nov 14 - Nov 15
Total with taxes and fees
New renovation cozy house in Worcester
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

Super 8 by Wyndham Sturbridge

Super 8 by Wyndham Sturbridge

10/10 Excellent
"Loved it beautiful view of the leg"
Luis 2-night trip
Posted 1 day ago
Super 8 by Wyndham Sturbridge

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 $157 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 8 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.