Holiday Rentals in Woodstock

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Holiday Rentals in Woodstock

Streamside Cottage Walking Distance to Town of Woodstock
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (194)
"My sister and I needed a quick getaway from the world and found refuge in this sweet little cottage that is right on the creek. The cottage was pristine, fully eqipped, quiet and tastefully decorated. My communication with the owner, Jane, was "easy breezy". Our favorite part of our stay were the sights and sounds of the water! It was truly magnificent. We came to the cottage a little tired from the pressures of life but left rejuvenated and filled with peace. Our short stay was delightful. We...
The price is €305
per night
13 May - 14 May
Streamside Cottage Walking Distance to Town of Woodstock
Romantic Luxury Chalet With Private Pool
1 bedroom, free WiFi, bed sheets
Romantic Luxury Chalet With Private Pool
10.0 out of 10, Exceptional, (259)
"Richard was very kind and thoughtful. The stay was very comfortable and Richard provided many ideas for things to in the vicinity. We will definitely consider staying here again if we're back in the area."
Romantic Luxury Chalet With Private Pool
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
"this was one of the most comfortable, easy to navigate vacation homes we have ever had. we used the grill, kitchen had everything you need, the deep sinks made washing dishes easy, (there was a dishwasher. but we didn't use it), windows allowed a 180 degree view of the back yard and forest beyond, where we saw a family of deer. Everyone slept like babies on mattresses that were heavenly! Or was super available and responsive to questions. A hannaford super market is 2.3 miles away. Bread Alone...
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
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HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
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
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
Terrace/patio
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
10.0 out of 10, Exceptional, (6)
"Property was updated and clean. Good location for hikes. The hot tub was enjoyable. Minimal kitchen tools and utensils. Plan ahead if you are cooking. Close to super market and dollar general if you forget some bits. Good location to pop into downtown."
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
1 bedroom, iron/ironing board, free WiFi, bed sheets
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
10.0 out of 10, Exceptional, (8)
"I’d absolutely recommend this stay for everyone. The loft is very homey. The spa bathroom is to die for. There’s such a cute coffee/tea station! And the area is in a cute little peaceful town. Checking in and out was very simple. They give detailed directions which I appreciated."
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
Cozy Relaxing Retreat in Saugerties, NY
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (29)
"The accommodations were excellent. We were a couple, but the house would be great for two couples. We loved the setting! The host has thought of everything, and the place is equipped to the max. Just bring yourself! Perfect location to explore the area."
Cozy Relaxing Retreat in Saugerties, NY
Mid-Century DJ’s Dream
Property grounds
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (13)
"Our stay was quite nice, the place looked as the pictures showed it to be which is just amazing. everything was music themed and our host had an amazing selection of vinyls. The only complaints I would say I had was the small flying bugs near the Tv and we weren’t provided paper towels. Overall it was a nice place for the night and the property itself was beautiful."
The price is €204
per night
14 May - 15 May
Mid-Century DJ’s Dream
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Property grounds
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (81)
"We enjoyed our stay at this property. The location is very private and comfortable. The kitchen is well stocked with amenities."
The price is €260
per night
21 May - 22 May
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (15)
"Matt is a wonderful host! I was very impressed by the cleanliness of the 1 bedroom cabin and how much thought went into providing guests with everything they need. I stayed for four nights and was very comfortable. The bed was so comfortable I slept great. Kingston is a city so some noise is expected. The neighborhood is very quiet at night and you can hear a little noise occasionally in the distance. Matt provides an adjustable sound machine. I put it on low and slept like a baby. Matt is very...
The price is €208
per night
21 May - 22 May
Campfire Cottage: Fireplace, fire pit & no chores!
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Property grounds
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
10.0 out of 10, Exceptional, (11)
"Perfect spot to visit grandkids Lots to do"
The price is €232
per night
21 May - 22 May
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Private kitchen
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
The Cabin at Chichester in the Catskills Mountains
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (164)
"Perfect"
The Cabin at Chichester in the Catskills Mountains
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
Aerial view
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
9.8 out of 10, Exceptional, (67)
"We travel to the Catskills at least once a year and stay at various locations. What sets this property apart is the true seclusion and absolutely no distractions from the nature around you. Even though it is close to hubs like Wyndham and Hunter (less than 20 to both) when sitting outside it feels like you are in the middle of nowhere. Inside is clean, cosey by the fire, and lots of fun things to do with our teenagers. Definitely would stay again."
Waterfront home w/swimming, kayaking and more; plus Hot Tub!!
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
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!
Beautiful House 0,5 Mile From Hunter Mountain
Exterior
Beautiful House 0,5 Mile From Hunter Mountain
9.8 out of 10, Exceptional, (188)
"It was a great family time. Play and rest"
Beautiful House 0,5 Mile From Hunter Mountain
Hamptons on the Hudson in South Saugerties
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
Hotel Woodstock - Iris suite
1 bedroom, internet, bed sheets
Hotel Woodstock - Iris suite
9.6 out of 10, Exceptional, (45)
"Cool propertry in a unique town"
The price is €209
per night
14 May - 15 May
Hotel Woodstock - Iris suite
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Outdoor spa tub
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!
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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

Streamside Cottage Walking Distance to Town of Woodstock
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (194)
"My sister and I needed a quick getaway from the world and found refuge in this sweet little cottage that is right on the creek. The cottage was pristine, fully eqipped, quiet and tastefully decorated. My communication with the owner, Jane, was "easy breezy". Our favorite part of our stay were the sights and sounds of the water! It was truly magnificent. We came to the cottage a little tired from the pressures of life but left rejuvenated and filled with peace. Our short stay was delightful. We...
The price is €305
per night
13 May - 14 May
Streamside Cottage Walking Distance to Town of Woodstock
The Herwood Inn
Exterior detail
The Herwood Inn
4.5 star property
9.8 out of 10, Exceptional, (32)
"The Herwood Inn was perfect. My wife and I were amazed. They truly thought of everything that you could possibly need. We loved it so much we are planning to rent out all the suites for a birthday weekend in the fall! "
The price is €227
per night
28 May - 29 May
The Herwood Inn
Woodstock Way Hotel
Superior Room, Fireplace, River View
Woodstock Way Hotel
4.0 star property
9.6 out of 10, Exceptional, (88)
"Relaxing environment and lovely rooms with view of the waterfall."
The price is €313
per night
13 May - 14 May
Woodstock Way Hotel
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 €204 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.

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 Woodstock Public Library and Woodstock Golf Club.

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

Hampton Inn Kingston

Hampton Inn Kingston

5/5 Excellent
"Very pleasant "
A verified traveller stayed at Hampton Inn Kingston
Posted 2 days ago
Hampton Inn Kingston