Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Holiday Rentals in Woodstock

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Children’s area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (44)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is HK$1,401
HK$2,354 total
includes taxes & fees
26 Oct - 27 Oct
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Streamside Cottage Half Mile to Town of Woodstock
Property grounds
Streamside Cottage Half Mile to Town of Woodstock
10.0 out of 10, Exceptional, (253)
"A beautiful quiet setting! "
Streamside Cottage Half Mile to Town of Woodstock
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Exterior
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
10.0 out of 10, Exceptional, (113)
"We loved our stay at this beautiful home in Woodstock. The house was even better than the pictures: it was spacious, clean, beautiful, and had all the amenities you could ask for. The locations was perfect- nicely secluded but extremely convenient. The owners were very helpful the whole time and were responsive every time we reached out."
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Starlite Motel
Exterior
Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, (270)
"The property was beautiful! Definitely coming back!"
The price is HK$973
HK$1,090 total
includes taxes & fees
14 Oct - 15 Oct
Starlite Motel
Sioux Tipi on Chloe's Lake
Exterior
Sioux Tipi on Chloe's Lake
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
The price is HK$856
HK$1,133 total
includes taxes & fees
19 Oct - 20 Oct
Sioux Tipi on Chloe's Lake
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.2 out of 10, Very good, (46)
"A quirky tiny cabin off the beaten path but in need of some upkeep, e.g. toilet not fully attached to the floor in the Tipi room, water has sulphur smell. We were only there for an overnight stay, and I sent a note once we were home, so hopefully the owners get a chance to fix things up! Pricey for its current condition."
The price is HK$973
HK$1,264 total
includes taxes & fees
15 Oct - 16 Oct
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Hamptons on the Hudson in South Saugerties
Terrace/patio
Hamptons on the Hudson in South Saugerties
10.0 out of 10, Exceptional, (31)
"Lovely property, well-maintained, clean and comfortable, and the host was especially responsive to all communications. Highly recommend."
Hamptons on the Hudson in South Saugerties
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons
9.8 out of 10, Exceptional, (92)
"Clean and perfect for a couple. Well maintained and provisioned. Yard/view is overgrown and view is obscured mostly by trees since the dwelling is ground level. But overall a pleasant stay in a quiet treed area. Would do again"
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
Exterior
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
10.0 out of 10, Exceptional, (18)
"The hosts are incredibly responsive and accommodating and the house is perfect for a group gathering. Setting is perfect, right on the river. "
The price is HK$3,145
HK$6,512 total
includes taxes & fees
20 Oct - 21 Oct
Big Indian near Full Moon Resort Spillian Onteora Mountain House Ski Belleayre
Rose Cottage
Outdoor dining
Rose Cottage
9.2 out of 10, Wonderful, (10)
"It's so peaceful there. It was lovely."
Rose Cottage
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Private kitchen
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
2.0 star property
The price is HK$1,100
HK$1,781 total
includes taxes & fees
19 Oct - 20 Oct
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Jessie's Harvest House
Bar (on property)
Jessie's Harvest House
10.0 out of 10, Exceptional, (2)
"For the location it is located it is a great place to stay. The rooms were clean and the beds and sheets were great. There is a restaurant on property so need to go far for something to eat. If I am ever in the area again I would definitely stay again. "
The price is HK$918
HK$1,574 total
includes taxes & fees
14 Oct - 15 Oct
Jessie's Harvest House
Sexiest Lil Cabin in Saugerties, NY
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY
9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
The price is HK$876
HK$1,155 total
includes taxes & fees
14 Oct - 15 Oct
Sexiest Lil Cabin in Saugerties, NY
The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (80)
"This was the perfect option for us for a nearby wedding. We ate twice at the River & Post (excellent) and went into Rhinebeck for the Sunday market. The property itself was very accommodating and had everything we needed. The kitchen was well equipped, beds comfortable, and plenty of seating options in the main room. The outside area was also a perfect place for coffee in the morning and we loved the chickens running around. Glenn could not have been nicer. Highly recommend!"
The Farm at Hyde Park
PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals
Dining
PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals
8.2 out of 10, Very good, (63)
"The home was nice and cozy. The owner was soo nice and soo responsive. Great place fo rent. "
PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Fridge, microwave, oven, stovetop
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
9.4 out of 10, Exceptional, (50)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
1 bedroom, free WiFi, bed sheets
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
10.0 out of 10, Exceptional, (94)
"We loved this stay! The yurt was absolutely charming! Such an amazing location within easy distance of hiking and the Empire State Trail bicycle path, plus great dining in New Paltz and Kingston."
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
9.6 out of 10, Exceptional, (25)
"Perfect spot to visit grandkids Lots to do"
The price is HK$946
HK$2,192 total
includes taxes & fees
14 Oct - 15 Oct
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Exterior
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (270)
"House was great. Plenty of beds, great kitchen and large table for all. Kitchen was well stocked. "
The price is HK$3,035
HK$7,203 total
includes taxes & fees
15 Oct - 16 Oct
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
9.8 out of 10, Exceptional, (31)
"Great location "
The price is HK$1,300
HK$2,723 total
includes taxes & fees
4 Nov - 5 Nov
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
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.
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Top Woodstock Hotel Reviews

Hotel Dylan

Hotel Dylan

10/10 Excellent
"Rooms are very functional, clean and and stylish. "
Francine 2-night trip
Posted 3 days ago
Hotel Dylan

Find out more about Woodstock

Search for holiday rentals in Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodstock using one of the methods below:

  • View our selection of featured holiday rentals in Woodstock
  • Use the map to find apartments and other holiday homes in the Woodstock neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodstock while they last

Look no further and take a look at our great range of rental properties in Woodstock!

Frequently asked questions

Are there holiday rentals 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. 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?

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock: This highly rated holiday home rental in Woodstock is located near skiing, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Woodstock?

Expedia has 68 holiday rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Enjoy the outdoors at Overlook Mountain Trailhead and Thorn Preserve - Catskill Center, or simply take in cultural attractions like Colony and SweetHeart Gallery. 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.