Holiday Rentals in Woodstock

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Holiday Rentals in Woodstock

Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (200)
"Very nice stay from start to finish. We stayed two nights after a busy conference and the space was clean and tranquil, with a gorgeous stream to relax us. "
The price is €344
per night
18 Jun - 19 Jun
Streamside Cottage Walking Distance to Town of Woodstock
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (32)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is €269
per night
16 Jun - 17 Jun
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (39)
"Junebug Cottage was a top notch place to stay and we enjoyed every minute of it! It is clean, well kept, and has everything needed for your stay. John is very hospitable and easy to communicate with. We loved the space and even spent some time reading on the back patio. Definitely recommend this place!"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
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Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (153)
"We had a great time, and the space was great. The house is so spacious, and that was perfect for us. We would have liked a few more towels, a bit more soap and shampoo, and the grill didn't get hot enough to cook the steak we had brought. Overall a wonderful time. Thank you very much."
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
The Farm at Hyde Park
9.8 out of 10, Exceptional, (49)
"We needed a central location for my daughter’s bridal shower. We could not have imagined a better place. It is beautiful and so natural. Glen was helpful and welcoming. He even came over to sweep off the expansive patio before our guests arrived and this was after he made sure everyone was awake. The house was well supplied with kitchen and dining items. The grounds were perfect - lawn chairs, picnic table, fire pit and free range chickens whose eggs we were able to enjoy. We would all stay here...
The Farm at Hyde Park
Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, (231)
"Good for the price. "
The price is €131
per night
17 Jun - 18 Jun
Starlite Motel
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
9.6 out of 10, Exceptional, (163)
"The house was fantastic. Close to Hunter Mountain Ski Resort and a cute one street town. Peter and Lara had both wood burning stoves going for us when we arrived. The house is wonderful with a fun separate hang out place for the kids. Well equipped kitchen. Comfortable beds. Hot tub with wonderful views. All the firewood you could ever need. We will be back for sure!"
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (37)
"Our trip was amazing. We do it again again and again"
The price is €117
per night
16 Jun - 17 Jun
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (85)
"Everything was as described, instructions to the house were precise and the facility was exactly what we 2 couples) needed for a weekend of strolls in Woodstock and trails around. We cooked 2 dinners, kitchen and BBQ were great."
The price is €278
per night
20 Jun - 21 Jun
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Charming Artist's Retreat
10.0 out of 10, Exceptional, (114)
"This is our second time staying at the cottage. What beautiful weather in such a beautiful setting. Incredible motorcycle ride through the mountains. Thank you Maureen. Robin & Bruce"
Charming Artist's Retreat
Large 13 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville
8.6 out of 10, Excellent, (14)
"There were 26 of us for a nice family gathering. Plenty of bedrooms and beds. Only 2 showers for 26 people a little challenging. Kitchen facilities lacking materials as noted in the listing. Bring your own pots and pans. Hot tub and fire pit were a nice addition. All in all, worked out great."
Large 13 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub
10.0 out of 10, Exceptional, (12)
"We loved all the thoughtful touches and design details of this cozy cabin! P"
Pet-Friendly Cozy Cabin in the Catskills with Cedar Hot Tub
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (7)
"Really cute interior. Perfect for our stay while at the horse show "
Hamptons on the Hudson in South Saugerties
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
9.4 out of 10, Exceptional, (41)
"The house is decorated beautifully, and the view of the river is great. The beds and linens were soo comfortable. Would love to return in warmer weather to enjoy the outdoors 😀"
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
9.8 out of 10, Exceptional, (87)
"Beautiful place, view is prime. The outdoor fire is awesome, the perfect spot to gather around. The myriad games are such great things to have. We left once over 3 days/nights. Owner and manager are super friendly and made the process seamless. Would definitely stay here again."
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (16)
"An unassuming setting belies the well-appointed interior and thoughtful extras you’ll find within. Parking is tight but it is off-street and the location offers come-and-go convenience for exploring the area."
The price is €270
per night
23 Jun - 24 Jun
Campfire Cottage: Fireplace, fire pit & no chores!
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (33)
"Pictures can fool anyone but as my son and I entered this property on our first day, he raised his hand with a genuine smile of joy, uttering that in renting this house, I made a very good choice. He was visiting me from Germany for his birthday, and I wanted to spend some days away from NYC, in quiet, conversation, and cooking. Being there for five days provided for us a wonderful framework to spend time together, and the house is as inviting as the pictures suggest. Our only criticism is a...
Cozy Relaxing Retreat in Saugerties, NY
Updated Cabin on the Esopus
10.0 out of 10, Exceptional, (19)
"I had a really good experience with this cabin and the location. The owner lives on site, met me within two minutes of my arrival, and then gave me a brief and complete rundown of the property and the surrounding area highlights. Property sits on a beautiful stream and the large property is very well maintained. Inside of the cabin matches the photographs in the listing. A lot of outdoor activities near by. If you like hiking, there are really nice lakes and trailheads all along Route 214, which...
Updated Cabin on the Esopus
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
9.6 out of 10, Exceptional, (42)
"We decided on a trip to Hunter Mountain with our family and some of my sons friends. I came across this house and let me tell you the pictures do not do it justice it’s even better in person!! We were beyond happy with the house and the location…. The house was fully stocked with everything you could imagine. So much room for our group of 13 including our golden retriever! The kids and adults loved the game room some adults even had a Pac-Man competition. We will definitely stay at this house...
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
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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.

Other types of properties in Woodstock you may be interested in

Woodstock Way Hotel
4.0 star property
9.6 out of 10, Exceptional, (93)
"It was the perfect oasis for a weekend getaway."
The price is €351
per night
19 Jun - 20 Jun
Woodstock Way Hotel
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (200)
"Very nice stay from start to finish. We stayed two nights after a busy conference and the space was clean and tranquil, with a gorgeous stream to relax us. "
The price is €344
per night
18 Jun - 19 Jun
Streamside Cottage Walking Distance to Town of Woodstock
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (32)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is €269
per night
16 Jun - 17 Jun
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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.

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 €117 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

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Woodstock Music Shop, or you can select a more secluded option if you're looking for a relaxing stay. The forests and art scene are just a few reasons why tourists like Woodstock. Make sure you have time to check out the riverfront and mountain views during your trip.

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

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace: This highly rated holiday home rental in Woodstock is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Woodstock?

Expedia has 69 holiday rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Overlook Mountain Trailhead and Thorn Preserve - Catskill Center are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Woodstock Music Shop. You’ll find favourite places to visit such as Hunter Mountain and Catskill Mountains in the wider area.

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 offer amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for small groups.

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