Woodstock Holiday Rentals

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Holiday Rentals in Woodstock

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.2 out of 10, Wonderful, (15)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

9.8 out of 10, Exceptional, (63)
"Everything was great! Very clean & cozy. Perfect spot for a ski trip!"
The price is NZ$485
includes taxes & fees
4 Feb - 5 Feb
Perfect Getaway! Cozy, Modern condo & Convenient to Everything you will need.

Beautiful Myrtle Beach Condo with Amenities Galore

8.8 out of 10, Excellent, (162)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (42)
"My fiancé and I stayed here over Christmas break for 4 nights. Snowboarded on Killington for 3 of those days. We were in close proximity to not only the mountain, but the shops to get our boards waxed and restaurants/bars. Those restaurants/bars were essential as this rental unit only has a microwave and mini fridge (as advertised). But for a place to just kick back and relax, clean up, and sleep. It was in a prime location. The spa services were available to us and while we didn't get to use...
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (35)
"Convenient to Okemo. Has everything you need for a ski week or weekend! "
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (90)
"Our stay was nice and cozy! The condo held our family nicely and it had everything we needed— we especially loved the coffee bar. It was an easy drive into town and very picturesque. "
Beautifully renovated with fireplace and coffee bar

SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

10.0 out of 10, Exceptional, (163)
"Great location with trail access. The pool, sauna and steam room were great. Very clean and very convenient. Owners were very responsive and helpful."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (200)
"My family and I just returned from our New Years stay at “Cozy Cottage”. The home is beautifully appointed and equipped with everything you could possibly need. Waking up every morning in the sun room overlooking the lake was an absolute dream especially on a snowy day. The location is fantastic, as it’s a stones throw to Okemo, and about a 7 min drive to the town of Ludlow where you will find a grocery store, quaint shops, and dining. We definitely plan to return!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (165)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (19)
"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.6 out of 10, Excellent, (26)
"We were a bit disappointed with this property. The pictures are a bit misleading as it felt dark and stuffy, which we didn’t expect. There was a strong cigarette odor that was hard to adjust to and the room kept dropping down to very cold temperatures (50s) even after we adjusted the thermostat. This was stressful since we have a 15 month old and were worried about her being too cold all night. The deck was completely blocked by a mound of treacherous ice from water dripping off the roof, which...
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (20)
"The place is everything it describes, however I missed the part where the bathrooms are in a separate building and they are shared. Thankfully for us there was nobody else staying there. Everything was very clean. Other than that I was satisfied. "
The price is NZ$327
includes taxes & fees
27 Jan - 28 Jan
Treehouse at Wise Pines- SoBo

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (198)
"We had a great stay. Cabin was cozy and warm while it was cold and blustery outside. Hot tub was a welcome perk. Bed was comfy. Regulating the heat upstairs took a littlelittleexperimentation.but we gor it. Stairs are steep! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

7.6 out of 10, Good, (50)
"This cozy cabin was perfect for a ski weekend with friends. We really enjoyed gathering by the stone fireplace after a couple long days out on the slopes."
The price is NZ$931
includes taxes & fees
5 Feb - 6 Feb
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Amazing Mountain Condo - Right across the street to Killington Resort

9.8 out of 10, Exceptional, (168)
"It was cozy, clean, and in the greatest location. "
Amazing Mountain Condo - Right across the street to Killington Resort

Comfortable mountain gem with pool, mountain views, & indoor parking space

8.4 out of 10, Very good, (26)
"This is a perfect property very close to the Snowden lodge. Easy access and perfect size. Great amenities. Will definately stay here again."
The price is NZ$661
includes taxes & fees
28 Jan - 29 Jan
Comfortable mountain gem with pool, mountain views, & indoor parking space

PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views

8.6 out of 10, Excellent, (8)
"Loved the room and resort. Everyone is very friendly and the room was perfect for 2-4 people. Has everything you need for a ski trip! "
PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (155)
"Enjoyed our stay. 5 minute drive to Jackson gore base made it nice to go back and forth with kids. Ursula was very attentive and did her best to make sure everything was in good order. "
Idyllic Lakefront House Suited Two Families

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.2 out of 10, Very good, (34)
"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
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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Other types of properties in Woodstock you may be interested in

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (498)
"Definitely a quaint and nice property. Spa didnt have availability so book super early "
The price is NZ$736
includes taxes & fees
9 Feb - 10 Feb
Woodstock Inn & Resort

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (712)
"We had a premium king room which was lovely. It had a balcony and the room overlooked the river, fields and mountains. We stayed there for 4 nights. The rooms are not serviced during your stay. However, you can request clean towels etc if you need them. "
The price is NZ$282
includes taxes & fees
29 Jan - 30 Jan
The Shire Woodstock

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (449)
"The suite was lovely and spacious. Perfect for a family trip away"
The price is NZ$247
includes taxes & fees
28 Jan - 29 Jan
Sleep Woodstock Motel
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.

Frequently asked questions

Are there holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to Red Wagon Toy Company, 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?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of Woodstock is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 30 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 Green Mountain National Forest and Marsh-Billings-Rockefeller National Historical Park are a couple of picturesque spots to enjoy the outdoors. While here, Saskadena Six Ski Area and VINS Nature Center 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.