South Woodstock Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in South Woodstock

Exterior
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodstock
9.8 out of 10, Exceptional, (228)
"Lovely property. Peaceful and beautiful surroundings."
United States
Karen G.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
Killington
9.0 out of 10, Wonderful, (53)
"Clean and beautiful scenery "
United States
David
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Indoor pool
Mountain Green

Mountain Green

2.0 star property
Killington
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
The price is ￥29,908
￥40,121 total
includes taxes & fees
Dec 7 - Dec 8
Mountain Green
Property grounds
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is ￥13,957
￥42,769 total
includes taxes & fees
Dec 16 - Dec 17
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
1 bedroom, free WiFi, bed sheets
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

2.5 star property
Rutland
10.0 out of 10, Exceptional, (2)
"Absolutely adored our stay! The cabin was cozy and had everything we could need and the hot tub was a huge plus after a long day of snowboarding. Would definitely come back!"
United States
Erin M.
The price is ￥23,262
￥29,875 total
includes taxes & fees
Dec 14 - Dec 15
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Exterior
Killington Retreat

Killington Retreat

2.0 star property
Killington
9.8 out of 10, Exceptional, (17)
"It was clean and check-in was simple. "
United States
David M.
Killington Retreat
Fridge, microwave, oven, stovetop
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

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

Ludlow
8.0 out of 10, Very Good, (41)
"Plenty of space and the two living rooms are great because the upstairs living room is very small."
United States
Brad H.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Property grounds
Idyllic Lakefront House Suited Two Families

Idyllic Lakefront House Suited Two Families

Ludlow
9.6 out of 10, Exceptional, (171)
"House and grounds were well maintained. "
United States
Dorothy Y.
Idyllic Lakefront House Suited Two Families
Smart TV, fireplace, video games, DVD player
The Cabin that brings people together

The Cabin that brings people together

Bridgewater
9.6 out of 10, Exceptional, (82)
"This was our 3rd visit for an annual family reunion. Nice house with great space, and the yard is a great space to really spread out. The manager is very responsive and checks in periodically; they really want you to have a great stay. I highly recommend this vacation rental, and we’ll be back!"
United States
Peter L.
The Cabin that brings people together
Interior
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cavendish
10.0 out of 10, Exceptional, (30)
"Beautiful property and excellent accommodations"
United States
Anthony W.
The price is ￥33,958
￥57,043 total
includes taxes & fees
Dec 9 - Dec 10
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
TV, fireplace, DVD player, books
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE

Killington
9.6 out of 10, Exceptional, (92)
"This condo provided everything we needed for a nice stay of skiing. We very much enjoyed our stay."
United States
Shawn C.
Ski right to your newly remodled great condo, enjoy woodburning fireplace & SAVE
Indoor pool
Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen

Killington
8.4 out of 10, Very Good, (38)
"Easy access to Killington Mountain "
United States
Dave S.
The price is ￥26,169
￥62,995 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy condo on ski shuttle route with free WiFi & full ktichen
Indoor pool
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

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

Killington
8.2 out of 10, Very Good, (38)
"Room was constantly too hot. Otherwise a great stay"
United States
Cameron M.
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Fridge, microwave, oven, stovetop
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington
9.8 out of 10, Exceptional, (60)
"Ski in/ Ski out Great locationJoel was very helpful and friendly. Really enjoyed our stay. "
United States
cynthia c.
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Exterior
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

killington
9.6 out of 10, Exceptional, (17)
"Great place to stay. Central location, bedrooms spacious and common areas w/plenty of space to hang out."
United States
Scott B.
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
Killington
9.4 out of 10, Exceptional, (16)
"Very nice stay."
United States
Marianne H.
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
Outdoor dining
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Mount Holly
9.8 out of 10, Exceptional, (226)
"It was our summer vacation with our family to Vermont and it happens to be our most favorite place to go! We loved the cabin. It was so cute and we enjoyed our stay! Vermont is a place to unwind and relax…..it’s our home away from home! "
United States
Kristen K.
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Property grounds
Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo

Woodstock
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
The price is ￥23,262
￥29,003 total
includes taxes & fees
Dec 16 - Dec 17
Treehouse at Wise Pines- SoBo
Property grounds
Winterplace at Okemo

Winterplace at Okemo

4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (26)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
United States
Kathia
Winterplace at Okemo
Golf
Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location

Ludlow
8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
United States
C A.
The price is ￥15,421
￥36,296 total
includes taxes & fees
Dec 17 - Dec 18
Efficient condo near slopes with kitchenette & great location
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Woodstock Hotel Reviews

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"Everything was excellent"
John 1-night trip
Posted 2 days ago
Comfort Inn Rutland - Killington

Find out more about South Woodstock

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

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

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

Frequently asked questions

Can I find vacation rentals in South Woodstock?

Yes, we offer vacation rentals near well known points of interest in South Woodstock, or you can choose a more remote option if you're looking for relaxation. Our travelers 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 vacation rentals in South Woodstock?

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable: This vacation home rental outside of South Woodstock is located in the city center and has a fireplace, a patio, and laundry facilities 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

How many vacation rentals are there in South Woodstock?

Choose from 5 Expedia vacation rentals in South Woodstock for a memorable vacation.

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 Marsh-Billings-Rockefeller National Historical Park. In the larger area, you’ll find VINS Nature Center and Woodstock Town Hall Theatre.

What’s a vacation rental in South Woodstock like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in South Woodstock. Vacation rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.