Photo by George Sykes

South Woodstock Vacation Rentals

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Vacation Rentals in South Woodstock

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Mountain Green

2.0 star property
6.4 out of 10, (9)
"We had a great time-- the apartment was clean and cute and the linens fresh. "
The price is CA $303
CA $406 total
includes taxes & fees
Apr 13 - Apr 14
Mountain Green

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (205)
"this cabin was absolutely adorable. The kitchen was great size living room, small but cozy. The only thing I think we would like to call out is that the stairs to the loft bedrooms are quite steep be very careful. Everything was impeccably, clean, very cozy and comfortable. Hot tub was perfect and all instructions for both of the hot tub and exit were clear and easy to read."
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (100)
"We had a wonderful stay at Wanda and Eran's condo in Quechee. The home was beautiful, very clean, and looks just like the photos. The kitchen is well stocked with dishes, pots and pans and spices/cooking oils. Wanda was extremely helpful with restaurant suggestions, local activities and was very responsive."
Beautifully renovated with fireplace and coffee bar

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

8.4 out of 10, Very good, (29)
" Convenient location right off Killington Rd. Short drive to ski or restaurants. One bar/restaurant on site- Vermont Craft. Newly renovated studio, clean on arrival. Check-in as described, did not need to contact host during stay. Thorough details provided in pre arrival communications. "
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

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

9.8 out of 10, Exceptional, (206)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

8.6 out of 10, Excellent, (17)
"Thanks for everything "
The price is CA $161
CA $500 total
includes taxes & fees
Apr 13 - Apr 14
Mountain Green Resort with Free WiFi and Full Kitchen — Walk to Slopes

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

9.2 out of 10, Wonderful, (38)
"My favorite place to stay in the area. Love it! "
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

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 CA $201
CA $250 total
includes taxes & fees
May 11 - May 12
Treehouse at Wise Pines- SoBo

Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

9.2 out of 10, Wonderful, (27)
"Perfect location for a ski trip to Okemo! Very close to the mountain and shops in town. Hot tub was great!"
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (25)
"Very friendly costumer service, we arrived late and we're greated with kindness. "
Solitude Village at Okemo

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

9.0 out of 10, Wonderful, (70)
"Unit is comfortable, clean and very accessible to the Clock tower base of Okemo mtn for skiing. That's why you choose this unit. It definitely can use some updates and general maintenance. Items homeowner could address:Shower drainage issues, several lightbulbs need changing, add some cutlery (There should be enough spoons to cover the amount of people the unit can accomodate), Update lockbox and the door lock on ski closet. "
The price is CA $105
CA $369 total
includes taxes & fees
Apr 14 - Apr 15
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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

3.0 star property
9.8 out of 10, Exceptional, (7)
"The location of this unit was ideal for people who like to vacation without having to drive. We literally skied to The Sunrise Cafe for dinner the first night. All of our outdoor adventures started right from our door with excellent access to trails. The Community center had a great hot tub and free equipment to use. We would definitely go back. "
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

Charming Lakefront Cottage on Lake Mascoma

10.0 out of 10, Exceptional, (5)
"Beautiful location, easy to get to. Gorgeous main floor with open floor plan and loads of nice design touches. Bedrooms are great. There's a nice little space adjacent to the LR with childrens books, games and toys, which kept our 18 month grandson busy. We skiied Mt Sunapee only 30 min away. highly recommend "
The price is CA $307
CA $718 total
includes taxes & fees
Apr 17 - Apr 18
Charming Lakefront Cottage on Lake Mascoma

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

8.0 out of 10, Very good, (39)
"Really awesome hot tub. The Jets were the strongest Jets I’ve ever felt. I loved it. It’s about a four or five minute walk in ski boots to get to the trail.House was adequately stocked for cooking. I do always bring my own pans and knives.They need to restock the forks apparently everybody must’ve thrown them in the garbage. Overall, great house I’d recommend it for families with kids."
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

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

8.4 out of 10, Very good, (29)
"I would recommend to friends and family "
The price is CA $74
CA $380 total
includes taxes & fees
Apr 13 - Apr 14
Comfortable mountain gem with pool, mountain views, & indoor parking space

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"Overall great stay for the family and friends. Communication was easy and available as needed. One issue that arose with people in the studio was handled expeditiously by Dave. Great location and layout for kids and adults to have separate areas. Would highly recommend "
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (11)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

9.6 out of 10, Exceptional, (20)
"Great place for our guys weekend. Place was clean and beds were comfortable. Would definitely rent again."
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

Quaint lakefront home with a private deck, firepit, and dock

9.4 out of 10, Exceptional, (93)
"We rented this property to be close to skiing at Okemo. Here are things we wanted to share:Location: it's a 5 minute drive to Okemo - fantastic! The cottage is at the base of Lake Pauline, directly across from a busy road. The road noise was noticeable, and it was winter with windows closed. It was not a secluded cabin in the woods.Check in: the code did not work. When we contacted Vacasa, we were told that they could reset the door code remotely. The back door was not locked, so we got in...
Quaint lakefront home with a private deck, firepit, and dock
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, (1005)
"."
The price is CA $171
CA $188 total
includes taxes & fees
Apr 13 - Apr 14
Comfort Inn Rutland - Killington

Align Inn Vermont

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Great option for Quechee!!"
The price is CA $151
CA $166 total
includes taxes & fees
Apr 27 - Apr 28
Align Inn Vermont

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (508)
"Wood fireplace in the lobby a lot of seating areas. The staff was excellent. Excellent food."
The price is CA $415
CA $517 total
includes taxes & fees
Apr 27 - Apr 28
Woodstock Inn & Resort
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 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?

Beautifully renovated with fireplace and coffee bar: This vacation home rental outside of South Woodstock is located on a river and has an outdoor pool, a fireplace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Woodstock Town Hall Theatre and Billings Farm and Museum.

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.