Woodstock Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Woodstock

Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (198)
"Spent two nights and wanted a place where we could easily bike into town and got exactly that! The sound of the creek outside was so relaxing, accommodations were clean and comfy. Definitely would return!"
The price is NZ$523
includes taxes & fees
27 May - 28 May
Streamside Cottage Walking Distance to Town of Woodstock
View from property
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!
Property grounds
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 NZ$456
includes taxes & fees
2 Jun - 3 Jun
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Save an average of 15% on thousands of hotels when you're signed in
Exterior
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (37)
"A perfect location and the cottage was set up with great attention to detail. Everything was very clean and comfortable. The property is beautiful too. John and Mollie are very responsive hosts and provided us with anything we needed. Could not ask for more. Highly recommend!"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (48)
"We thoroughly enjoyed our stay. It was a unique setting. Glen was very accommodating for our check in & out needs. Great location & central to everything we wanted to do & see. Definitely would come back."
The Farm at Hyde Park
Property grounds
'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 NZ$237
includes taxes & fees
29 May - 30 May
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (83)
"A perfect getaway retreat! Gorgeous grounds with garden, firepit with adirondack chairs, flowers and tree-li ed view as far as the eye can see from upper and lower decks equipped with seating, umbrella shade and dining area with bbq grill. All the comforts of home--and that's before you enter!! The home is very clean, bright with A-frame windows in the family room Updated kitchen and fine wood flooring as well as beautiful bathrooms. Downstairs bedrooms were small but had very comfortable...
The price is NZ$513
includes taxes & fees
20 Jun - 21 Jun
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Exterior
Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, (229)
"Good for the price. "
The price is NZ$229
includes taxes & fees
27 May - 28 May
Starlite Motel
Fridge, microwave, oven, stovetop
Charming Artist's Retreat
10.0 out of 10, Exceptional, (113)
"From beginning to end a pleasant stay. Owner was on contact to make sure everything was in order. Fresh cut flowers, plenty of clean white fluffy towels, comfortable bedding and the view through sparkling clear windows. What a wonderful way to spend the mother's day weekend with my daughter and spend some time outdoors exploring little Hudson river towns. 10 thumbs up!!!!"
Charming Artist's Retreat
Terrace/patio
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
10.0 out of 10, Exceptional, (7)
"House and location were great, would definitely come back."
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (31)
"The house is secluded and peaceful with a huge deck for a cool breeze with morning coffee or an evening glass of wine. The house was spotless and well equipped with anything you could possibly need. Restaurants, grocery, and Katterskill Falls for hiking all within a 15-20 minute drive. Our host, Nick, was very attentive making sure everything was as we expected ( and it was). Would stay here again if the opportunity arises. I highly recommend this property for your vacation getaway."
Cozy Relaxing Retreat in Saugerties, NY
Outdoor dining
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
9.8 out of 10, Exceptional, (86)
"Stayed here with a group of friends, and loved it! We had terrible weather, but the house was the best place to be stuck inside. We made pizzas in the outdoor oven, and enjoyed the hot tub. Can't recommend enough! The property manager Alan was awesome."
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
Exterior
Beautiful House 0,5 Mile From Hunter Mountain
9.8 out of 10, Exceptional, (189)
"It was a great family time. Play and rest"
Beautiful House 0,5 Mile From Hunter Mountain
Property grounds
Updated Cabin on the Esopus
10.0 out of 10, Exceptional, (18)
"The cabin was excellent, very clean, and they gave us everything we needed"
Updated Cabin on the Esopus
Fridge, microwave, oven, stovetop
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 NZ$336
includes taxes & fees
28 May - 29 May
Campfire Cottage: Fireplace, fire pit & no chores!
Exterior
The Studio at the Inn at High Falls
8.4 out of 10, Very good, (17)
"Love staying at The Studio at the Inn at High Falls. It truly is my new home away from home. Soo Clean, Comfortable and incredible friendly helpful people who own and work there. Again Thank you Frank and too a New Year. Patricia"
The price is NZ$424
includes taxes & fees
2 Jun - 3 Jun
The Studio at the Inn at High Falls
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (165)
"Very clean, good area"
The Cabin at Chichester in the Catskills Mountains
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (6)
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
Property grounds
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
9.8 out of 10, Exceptional, (18)
"My recent weekend getaway to the Catskills was truly unforgettable, thanks to our wonderful host and their charming retreat nestled in the heart of this picturesque mountain region. From the moment we arrived, we were greeted with warm hospitality and a sense of tranquility that immediately set the tone for our stay. The accommodations were nothing short of perfect – cozy yet spacious, with rustic charm and modern amenities seamlessly blended together. Our host went above and beyond to ensure...
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
Don't see what you're looking for?
See all available properties in Woodstock
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

Superior Room, Fireplace, River View
Woodstock Way Hotel
4.0 star property
9.6 out of 10, Exceptional, (91)
"We really enjoyed the stay at Woodstock Way Hotel. It was extremely clean, easy to find and the rooms were immaculate. The design Was a true seller for us as art and accommodations meet. Just excelllent. "
The price is NZ$613
includes taxes & fees
2 Jun - 3 Jun
Woodstock Way Hotel
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (198)
"Spent two nights and wanted a place where we could easily bike into town and got exactly that! The sound of the creek outside was so relaxing, accommodations were clean and comfy. Definitely would return!"
The price is NZ$523
includes taxes & fees
27 May - 28 May
Streamside Cottage Walking Distance to Town of Woodstock
Exterior detail
The Herwood Inn
4.5 star property
9.8 out of 10, Exceptional, (33)
"Everything was great. Anything you want is there. Books, Records, Ice, Coffee ☕."
The price is NZ$418
includes taxes & fees
28 May - 29 May
The Herwood Inn
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.

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 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. Other places in town to visit include Karma Triyana Dharmachakra Monastery and Woodstock Public Library.

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.

Recent reviews of Woodstock properties
Expedia verified reviews