Woodstock Holiday Rentals from NZ$355: Search Short-Term Rentals

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Our top choices for Woodstock holiday rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

1. Fat Sheep Farm & Cabins

Windsor

Jessica

includes taxes & fees

3 Nov - 4 Nov

A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

2. Bridgewater Living - Ben&Jerry Suite

Bridgewater

Sylvia F.

includes taxes & fees

1 Nov - 2 Nov

A sunroom with wicker furniture, large windows, and string lights.

3. Addie's Place: A Quiet and Quirky Guesthouse

Hartford

Victor R.

includes taxes & fees

28 Oct - 29 Oct

A bedroom with two beds, a door, and a small table with a lamp.

4. Bridgewater Living - Ski VT Suite

Bridgewater

includes taxes & fees

2 Nov - 3 Nov

A large indoor swimming pool with clear lanes, wooden beams, and seating areas.

5. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Hartford

Nina S.

includes taxes & fees

28 Oct - 29 Oct

A person standing on a sandy beach by a river with trees in the background.

6. Cabin on the hill Ascutney Vt - 4 bedrooms

West Windsor

Alvin

includes taxes & fees

7 Oct - 8 Oct

A compact kitchen with a refrigerator, stove, microwave, and sink.

7. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

Plymouth

includes taxes & fees

5 Oct - 6 Oct

A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

8. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Killington

Spencer P.

includes taxes & fees

5 Oct - 6 Oct

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Top Woodstock Hotel Reviews

Fireside Inn & Suites West Lebanon

10/10 Excellent

"What a great find! Close to shopping and restaurants. Great complimentary breakfast buffet. Lovely lobby with fireplace."

The Shire Woodstock

10/10 Excellent

"We had Deluxe King River view - deluxe has a fireplace and shares a balcony with rocking chairs. The room was great except a couple little maintenance issues (I told the front desk and hope they fix). And it’s a great location walkable to downtown, great views of river and hills, and the inn has fire pits ready to go. Too bad coffee makers are in the hallway, not in the room, and there’s no breakfast (they said they might start next year). We went nearby for breakfast, and a good market is just across the street."

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"

On The River Inn

8/10 Good

"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."

Woodstock Village Carriage House

8/10 Good

"Great location, the unit was simple, allowed us to walk to town and the grocery store.The only confusion was the outdoor space. Property is beautiful, we were unsure if we could sit by a pool on the property as that was not listed in the marketing material. As a result, we did not find any outdoor space that we could enjoy."

Deer Brook Inn

10/10 Excellent

"What an amazing place! The room was perfect--comfy bed, luxurious bedding and great amenities. As a guest, you have full access to the living room, dining room and outdoor areas--which includes a fire pit and sauna. Breakfast was delicious with locally sourced products--many from the property itself--including edible flowers. The host was friendly, welcoming, and just a delightful person. And so very thoughtful. Would definitely stay here again and highly recommend!"

Find out more about Woodstock

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Woodstock holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Woodstock. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Woodstock. Seeing all the best attractions is bound to make you fall in love with Woodstock. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Woodstock short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Billings Farm and Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Woodstock. Make sure you allow time to enjoy the riverfront during your holiday.

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

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town: This highly rated holiday home rental in Woodstock is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind. Another good choice for your trip to Woodstock is Classic, cozy farmhouse in the 4 season playground of VT's prettiest town!.

How many holiday rentals are there in Woodstock?

Expedia has 37 holiday rentals for your stay in Woodstock.

What’s there to see and do in Woodstock?

Cultural attractions include Woodstock Town Hall Theatre and Billings Farm and Museum, whereas Marsh-Billings-Rockefeller National Historical Park and Lakota Lake are a couple of picturesque spots to enjoy the outdoors. While here, Saskadena Six Ski Area and Green Mountain National Forest are other places worth a visit.

What’s a holiday rental in Woodstock like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Woodstock. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Woodstock holiday rentals

1. Fat Sheep Farm & Cabins

2. Bridgewater Living - Ben&Jerry Suite

3. Addie's Place: A Quiet and Quirky Guesthouse

4. Bridgewater Living - Ski VT Suite

5. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

6. Cabin on the hill Ascutney Vt - 4 bedrooms

7. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

8. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

9. Welcoming condo near the slopes with free WiFi and full kitchen

10. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

11. 180-degree panoramic views of Vermont's mountains from the living room and Deck

12. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

13. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

14. The Suites at Killington Center

15. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

16. Killington resort: Walk to Mountain, Bike, Pool

17. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

18. CozyCub -Location, Fireplace, Ski Off/ Shuttle On

19. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

20. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

Find holiday rentals that suit your style

Top Woodstock Hotel Reviews

Fireside Inn & Suites West Lebanon

The Jackson

The Shire Woodstock

Jackson Gore Village, A Vail Resorts Property

On The River Inn

The Vesper

Lincoln Inn & Gallery

Woodstock Village Carriage House

Deer Brook Inn

Find out more about Woodstock

Frequently asked questions

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