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In two weeks
19 Sep - 21 Sep
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
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26 Dec - 28 Dec

Vacation Homes in South Woodstock

Our top choices for South Woodstock vacation homes

Idyllic Lakefront House Suited Two Families
Property grounds

Idyllic Lakefront House Suited Two Families

9.6 out of 10, Exceptional, (165)
"We really enjoyed our stay at the lake house. We had great views of the lake and the kitchen was very well stocked. The beds were comfortable and the house was very clean and nicely decorated. Thank you for the incredible stay and we will be staying again!"
Idyllic Lakefront House Suited Two Families
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Property grounds

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (38)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Converted Carriage Barn | The Carriage House Unit1
Dining

Converted Carriage Barn | The Carriage House Unit1

9.8 out of 10, Exceptional, (21)
" Very nice and quiet location. Close to various restaurants. Enjoyed our stay!"
Converted Carriage Barn | The Carriage House Unit1
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Exterior

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

9.8 out of 10, Exceptional, (175)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Terrace/patio

Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak

2.0 star property
9.8 out of 10, Exceptional, (76)
"Beautiful area and gorgeous leaves. Liked having a weber grill."
Charming waterfront 2BR house, private beach, waterfall, firepit, wifi, kayak
Beautifully renovated with fireplace and coffee bar
Smart TV, fireplace, books

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (115)
"My husband and I came from Michigan and met family from Massachusetts to run the Covered Bridges Half Marathon! This spot was so perfect—we loved the coffee bar and just enjoyed how comfortable and homey the whole place feels. We would stay here again in a heartbeat!"
Beautifully renovated with fireplace and coffee bar
Custom-built Tiny House on forested lot near Quechee
Fridge, microwave, oven, stovetop

Custom-built Tiny House on forested lot near Quechee

9.8 out of 10, Exceptional, (60)
"Arturo and John are incredibly thoughtful and attentive hosts. They have considered every possible need and detail in the space. It’s beautiful, homey, and full of personality. The hot tub is a dream. We loved the location. It was easily to get to Woodstock, restaurants, and sightseeing, while still feeling remote and secluded. 10/10 would stay here again! "
Custom-built Tiny House on forested lot near Quechee
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Fridge, microwave, oven, stovetop

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (55)
"Cozy accommodations, great location, beautiful property, wonderful hosts."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Ski Chalet with Hot Tub on Okemo Mountain
Outdoor spa tub

Ski Chalet with Hot Tub on Okemo Mountain

10.0 out of 10, Exceptional, (45)
"Wonderful House - Held 2 Families Perfectly3 min drive to mountain The hot tub is great addition "
Ski Chalet with Hot Tub on Okemo Mountain
Converted Carriage Barn | The Carriage House Unit2
Interior

Converted Carriage Barn | The Carriage House Unit2

9.6 out of 10, Exceptional, (4)
"Very cool conversion of an old barn. Very comfy and rather iconic. Because of the barn construction, there was an occasional encounter with a bug or two. Nicely located with many shops and restaurants nearby. The surrounding neighborhood of Quechee is very pleasant and kind of upscale country. Be aware there are no hangers/closets/ironing board/washer/dryer, so plan accordingly."
Converted Carriage Barn | The Carriage House Unit2
Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
Smart TV, fireplace

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola

Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Fridge, microwave, oven, stovetop

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"Absolutely loved it!!! Amazing house. Will definitely stay again!"
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Exterior

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (36)
"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Exterior

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

9.8 out of 10, Exceptional, (126)
"Terrific and comfortable place to stay! Amazing firepit!"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
Exterior

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

9.8 out of 10, Exceptional, (37)
"Great property, cozy and well maintained!"
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fridge, microwave, oven, stovetop

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

8.0 out of 10, Very Good, (40)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Exterior

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

10.0 out of 10, Exceptional, (110)
"Nice rental for our family and the owner was very rsponsive."
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Exterior

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

9.8 out of 10, Exceptional, (222)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Country townhome - mountain view - walk to Village of Quechee - near Club & golf
Pool

Country townhome - mountain view - walk to Village of Quechee - near Club & golf

9.0 out of 10, Wonderful, (36)
"Great location, cute condo, comfortable beds, modern kitchen."
Country townhome - mountain view - walk to Village of Quechee - near Club & golf
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
Exterior

Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

10.0 out of 10, Exceptional, (48)
"Our family had a great stay in Ludlow for a four day ski vacation. Tom and Patti were great hosts and their home is convenient to both Okemo and Killington. The hosts communicated well with us and their place was perfect for our needs (family of 4), clean, and convenient to downtown Ludlow and restaurants. "
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!
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 South Woodstock Hotel Reviews