Photo by George Sykes

Holiday Rentals in South Woodstock

Check prices for these dates

Holiday Rentals in South Woodstock

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 €268
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, (161)
"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!

8.8 out of 10, Excellent, (40)
"Located next to everything in Killington and property was clean. Use of hot tub and pool was a plus. Will stay here again "
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, (34)
"Great weekend! Beautiful location !!"
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, (161)
"What a cute condo! It had everything we needed from cooking supplies to board games to sleds! The host was super kind to make sure we could arrive ahead of the New Years Eve celebration at K-1. We also checked out the sports club - indoor pool and hottub - which was nice. Plenty of wood meant we could have a nice fire roaring as the snow fell. Truly picturesque. We lucked out with fresh powder for ski on/off one day which was an adventure. If you enjoy quieter slopes, Sunrise is perfect. Sunrise...
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, (18)
"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

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

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 €186
includes taxes & fees
15 Jan - 16 Jan
Treehouse at Wise Pines- SoBo

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 €296
includes taxes & fees
15 Jan - 16 Jan
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, (167)
"Me and my daughter stayed for three nights and loved the condo! It was so cute clean and comfortable. We got on the shuttle right in front of the condo for a two minute ride to the main base of Killington resort. The first day we literally walked because it was so close. I highly recommend this condo!"
Amazing Mountain Condo - Right across the street to Killington Resort

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!!

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 €338
includes taxes & fees
21 Jan - 22 Jan
Comfortable mountain gem with pool, mountain views, & indoor parking space

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

8.4 out of 10, Very good, (7)
"Great location and the host was right on the money anytime I had a problem with question I was able to email them and they got right back to me. That’s the way to do it."
PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (89)
"Everything about this property was perfect for our family of 6! Location, charm and cleanliness, perfection! "
The price is €493
includes taxes & fees
21 Jan - 22 Jan
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

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
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 South Woodstock you may be interested in

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1008)
"Enjoyed my stay. A nice steakhouse next door too."
The price is €144
includes taxes & fees
20 Jan - 21 Jan
Comfort Inn Rutland - Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1001)
"Best staff EVER!! Tracy the manager is professional, caring, helpful, kind, and made our family trip our best ever. She is warm and made us feel at home and always helped us. Her front desk colleague Alex was so sweet and friendly. It was my birthday and he made sure that it felt special. So kind both of them. The housekeeping staff - Enrique and Adrian and others are helpful friendly always ready with an extra towel or a smile. Buffet staff for breakfast Kevin and others started our ski days...
The price is €236
includes taxes & fees
21 Jan - 22 Jan
Killington Mountain Lodge, Tapestry Collection by Hilton

Align Inn Vermont

2.5 star property
9.0 out of 10, Wonderful, (1009)
"This was a great value at a super convenient location coming from the south, if you’re heading up to Woodstock or Killington. The restaurant/bar next door has big portions of comfort food and is a fun local spot. The room was larger and more updated than I expected. "
The price is €116
includes taxes & fees
27 Jan - 28 Jan
Align Inn Vermont
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

Can I find holiday rentals in South Woodstock?

Yes, there are holiday rentals close to the most popular sights in South Woodstock, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say South Woodstock has a good selection of restaurants. Make sure you have time to check out the bars while you're in the area.

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

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location: This holiday home rental outside of South Woodstock is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 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 private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in South Woodstock?

Choose from 3 Expedia holiday rentals in South Woodstock for a memorable holiday.

What’s there to see and do in South Woodstock?

While exploring the area, visit family-friendly sights like Sugarbush Farm, or get outside and enjoy nature at Quechee Gorge Bridge. In the wider area, you’ll find Woodstock Town Hall Theatre and Billings Farm and Museum.

What’s a holiday rental in South Woodstock like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Woodstock. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to 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 an attractive choice for family trips.