Woodstock Vacation Rentals

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Our top choices for Woodstock vacation rentals

10.0 out of 10, Exceptional, (22 reviews)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
United States
Savanna
$542 nightly
The price is $614
Mar 1 - Mar 2
Total with taxes and fees
Stunning Lakefront Escape! Book Your Dream Getaway!
9.8 out of 10, Exceptional, (81 reviews)
"Lovely stay on the lake, we enjoyed the location and the kayaks on the lake. "
United States
Lucy H.
$564 nightly
The price is $639
Mar 1 - Mar 2
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
8.8 out of 10, Excellent, (48 reviews)
"It was great! Thank you :-) "
United States
Becki S.
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.4 out of 10, Exceptional, (30 reviews)
"Safe, inviting stay."
United States
Gabe M.
$244 nightly
The price is $276
Mar 1 - Mar 2
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
9.2 out of 10, Wonderful, (40 reviews)
"Pet and family, friendly"
United States
Mary-Kate G
$304 nightly
The price is $343
Mar 10 - Mar 11
Total with taxes and fees
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
9.2 out of 10, Wonderful, (27 reviews)
"Loved the views of the lake and the decor. "
United States
Beth L.
$331 nightly
The price is $375
Mar 1 - Mar 2
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
$271 nightly
The price is $310
Mar 1 - Mar 2
Total with taxes and fees
Beautiful 2-story Downtown Worcester king bed with Office
9.4 out of 10, Exceptional, (3 reviews)
"Very nice place. Quiet neighborhood and close to town. "
United States
michael C.
$165 nightly
The price is $187
Mar 8 - Mar 9
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam
9.6 out of 10, Exceptional, (33 reviews)
"Great location, beautiful view completely relaxing "
United States
Carlos T.
$222 nightly
The price is $252
Mar 8 - Mar 9
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
9.8 out of 10, Exceptional, (36 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.
$268 nightly
The price is $304
Mar 3 - Mar 4
Total with taxes and fees
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs
10.0 out of 10, Exceptional, (14 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$166 nightly
The price is $188
Mar 1 - Mar 2
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station

Vacation Home in North Grosvenordale

Wizard's Roost at Underhill Hollow
9.6 out of 10, Exceptional, (21 reviews)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
United States
Meghann H.
$166 nightly
The price is $188
Mar 8 - Mar 9
Total with taxes and fees
Wizard's Roost at Underhill Hollow
9.8 out of 10, Exceptional, (8 reviews)
"All and all a great place to stay."
United States
Anonymous traveler
$442 nightly
The price is $500
Mar 3 - Mar 4
Total with taxes and fees
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
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.
$231 nightly
The price is $261
Mar 2 - Mar 3
Total with taxes and fees
Spacious, unique barn with beautiful views.
9.6 out of 10, Exceptional, (14 reviews)
"Very nice country stay. "
United States
michael C.
$263 nightly
The price is $298
Mar 25 - Mar 26
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
9.4 out of 10, Exceptional, (20 reviews)
"Beautiful location. Great communication with host who continually checked in with us. Home had everything we needed to host my daughter and her friends for a great dinner for UCONN family weekend. Will definitely be back! "
United States
Michelle L.
$320 nightly
The price is $363
Mar 1 - Mar 2
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
8.6 out of 10, Excellent, (24 reviews)
"It’s very clean with lots of room for the price. The neighborhood is quiet and peaceful. The pool is well-maintained. The owner is very responsive and helpful. Highly recommend!"
United States
Jan L.
$837 nightly
The price is $884
Mar 2 - Mar 3
Total with taxes and fees
Spacious Getaway by TreeHouse Brewery & Amazon WareHouse
10.0 out of 10, Exceptional, (1 review)
"Perfect quiet place to work and rest"
United States
michael C.
$372 nightly
The price is $416
Mar 1 - Mar 2
Total with taxes and fees
Charming 1-bedroom apartment with AC, WiFi in pleasant Webster

Apartment in West Brookfield

Spacious Massachusetts Apartment #2
9.0 out of 10, Wonderful, (29 reviews)
"Really a cute place to stay, very clean and comfortable "
United States
Michelle J.
$269 nightly
The price is $300
Mar 6 - Mar 7
Total with taxes and fees
Spacious Massachusetts Apartment #2
$169 nightly
The price is $189
Mar 1 - Mar 2
Total with taxes and fees
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
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

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 $188 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.

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?

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 Roseland Park 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.