Woodstock Holiday Rentals from €102: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Woodstock has to offer?

Secluded 2-Acre Lakefront Home! Book Your Getaway! : This highly rated holiday home rental in Woodstock is located on a lake, and has a patio, a selection of games and a BBQ 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 that you can cook with friends or family.

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Our top choices for Woodstock holiday rentals

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

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

Woodstock

Emma S.

includes taxes & fees

27 Sept - 28 Sept

A house with a white porch, a black door, and a window with a white frame.

2. Cozy 1-bedroom cottage in serene Pomfret.

Pomfret

Bud n' Mary's Marina B.

includes taxes & fees

27 Sept - 28 Sept

A red building with a colorful mural on the front, a covered porch, and a stone foundation.

3. Wizard's Roost at Underhill Hollow

North Grosvenordale

Mateo A.

includes taxes & fees

29 Sept - 30 Sept

A bedroom with a wooden bed, large windows, and a view of greenery outside.

4. Rustic Farmette Studio with Hot Tub & Pool

Thompson

Lynn J.

includes taxes & fees

27 Sept - 28 Sept

A room with a sloped ceiling, wooden beams, a purple door, and a star decoration on the wall.

5. The Tree House at Underhill Hollow

Thompson

Douglas C.

includes taxes & fees

28 Sept - 29 Sept

A two-story house with a front porch, stone steps, and a driveway.

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

Putnam

Lucy L.

includes taxes & fees

22 Oct - 23 Oct

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.

7. SteamPunk Bunk House and Intergalactic Way Station

Thompson

Pauline S.

includes taxes & fees

8 Oct - 9 Oct

A wooden cabin with a glass upper floor, surrounded by a forest.

8. Dove Cabin up in the Trees

Holland

Maryann

includes taxes & fees

27 Sept - 28 Sept

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Top Woodstock Hotel Reviews

Publick House Historic Inn and Country Motor Lodge

10/10 Excellent

"My husband and I had a wonderful stay in the Chamberlin House. The staff was extremely helpful and kind. Our room was clean and very tastefully decorated, in an "updated" classic colonial style. The grounds were absolutely gorgeous and we thoroughly enjoyed a delicious dinner in the Publick House restaurant. The breakfast pastries in the onsite bakery were outstanding. We would never hesitate to stay at Publick House again."

Comfort Inn & Suites Sturbridge - Brimfield

8/10 Good

"We stayed in the motel rooms with our dog. The floor could've used a washing, but the bedding and bathroom were nice. The free breakfast was okay, but nothing to write home about. Swimming pool looked kinda sketchey, so we skipped that (pool looked really old). Very good location and places to walk the dog. One thing we really weren't happy about was there is no place to unpack our suitcases! 4 coat hangers, and no bureau or drawers so we lived out of our suitcases. TV had basic cable and channels were difficult to figure out. We could've done much worse, and we did enjoy our visit. Staff was very nice! Thank you."

Comfort Inn Auburn - Worcester

10/10 Excellent

"We spent five nights at the Days Inn in Auburn and had a wonderful experience. The staff made us feel right at home, and getting a freshly baked cookie when we arrived was such a thoughtful touch. We also really appreciated having coffee, decaf, and hot water for tea available throughout the day. It was so convenient to grab a cup whenever we wanted. A special shout-out to Neusa, who went above and beyond to make sure the breakfast area was always fully stocked and ready for guests. Her attention to detail and friendly service really made a difference! The bathrooms have also been remodeled, and we especially liked the extra room in the shower. Our stay was comfortable and relaxing, and everyone we encountered was friendly. We’d definitely stay there again when visiting Auburn. Highly recommend!"

Secluded 2-Acre Lakefront Home! Book Your Getaway!

10/10 Excellent

"Lovely, comfortable house in a beautiful setting. Everything is as described / matches the photographs. You walk down a beautiful slope to get to the water, there are four kayaks (and plenty of lifejackets), there is a huge deck as well as chairs down by the water. Recommend the Bigelow Hollow Breakneck Pond hike - it's gorgeous and just an 8-minute drive from the lake. We had a great stay! Thank you!"

Stunning Lakefront Escape! Book Your Dream Getaway!

10/10 Excellent

"We were in the area for a wedding at Willow Hill. This could not have been a better home base for the weekend. It was close to the venue, and the beautiful lakeside setting made it the perfect retreat when we weren’t tied up with wedding duties. The layout worked well for our party of six, and we would end each night on the expansive deck stargazing over a glass of wine. It"

Find out more about Woodstock

Everything you need to know about Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as €102 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday 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 holiday.

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 holiday rental in Woodstock?

Yes, there are holiday rentals close to the most popular sights in Woodstock, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Woodstock has to offer?

Secluded 2-Acre Lakefront Home! Book Your Getaway!: This highly rated holiday home rental in Woodstock is located on a lake, and has a patio, a selection of games and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Woodstock?

Expedia has 7 holiday 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 holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals feature extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for families.

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Our top choices for Woodstock holiday rentals

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