A rural landscape with rolling hills, a winding dirt road, and a cluster of red barns.

South Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for South Woodstock vacation rentals

Interior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (12 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
$229 nightly
The price is $259
Jul 19 - Jul 20
Total with taxes and fees
Addie's Place: A Quiet and Quirky Guesthouse
Beach

Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
$444 nightly
The price is $502
Jul 20 - Jul 21
Total with taxes and fees
Cabin on the hill Ascutney Vt - 4 bedrooms
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
$898 nightly
The price is $1,006
Jul 23 - Jul 24
Total with taxes and fees
Cozy Vermont Cabin · Mountain Views · Near Okemo
Interior

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
$543 nightly
The price is $608
Jul 26 - Jul 27
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish
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, (45 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
$306 nightly
The price is $333
Aug 4 - Aug 5
Total with taxes and fees
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Terrace/patio

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (13 reviews)
$312 nightly
The price is $349
Jul 30 - Jul 31
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (20 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$278 nightly
The price is $303
Jul 20 - Jul 21
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
$278 nightly
The price is $303
Jul 20 - Jul 21
Total with taxes and fees
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Outdoor pool, a heated pool

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
$480 nightly
The price is $538
Jul 18 - Jul 19
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Exterior

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
$229 nightly
The price is $259
Jul 18 - Jul 19
Total with taxes and fees
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (87 reviews)
"Beautiful and immaculately clean home located within walking distance to downtown, shopping, and restaurants. Very quiet location. We felt safe and comfortable at this home. Property has 3 bedrooms and 5 very comfortable beds. The attic bedroom has 3 single beds which is handy for larger families. Loved sitting around the fire pit and was pleased that our yard was separated from the neighbors. Thank you so much for sharing your hospitality."
United States
Kristen
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Coffee/tea maker, fridge, microwave, oven

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

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (113 reviews)
"Clean great cozy place!"
United States
Himanshu P.
$386 nightly
The price is $418
Jul 21 - Jul 22
Total with taxes and fees
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Interior

The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle

The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Ludlow
10.0 out of 10, Exceptional, (1 review)
"Cute place right in town, super convenient to the mountain (although if you’re relying on the shuttle it’s only once an hour so can be annoying if you don’t time it well). Rooms comfortably slept 4 plus one on the sofa bed, annd everything was in good shape, Andrew and Jillian were great hosts!"
United States
Max R.
$655 nightly
The price is $760
Jul 18 - Jul 19
Total with taxes and fees
The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle
Living area

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
$456 nightly
The price is $511
Jul 19 - Jul 20
Total with taxes and fees
Cozy Private Cabin in Andover - Fireplace & Hot tub
Terrace/patio

Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Cool building, right on main street. Building is undergoing renovation on back porches so some construction material and disruption. The kitchen was not well equiped and needs an update. However, the space is really cool, very open, big bedrooms, decent bedding. Shower is a little small but nice. Good value"
United States
jonathan w.
$357 nightly
The price is $403
Jul 21 - Jul 22
Total with taxes and fees
Okemo's Back Room - in the heart of the village on the shuttle route!
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
$325 nightly
The price is $355
Aug 16 - Aug 17
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
TV, fireplace, books, stereo

Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views

Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
Ludlow
10.0 out of 10, Exceptional, (1 review)
"My family and I stayed at this property last weekend and it was amazing!!! We were the first to rent as this is a brand new construction home. Everything inside is brand new from the bedding, furniture and amazing cookware. This house has a few great features that make it top notch: 1: Every bedroom has an en-suite bathroom, so we all had our own space and privacy. The bedrooms were big and beds were so comfortable. The master bedroom has this huge shower and tub that was so nicely designed. 2:...
United States
Michael
$1,706 nightly
The price is $1,928
Jul 18 - Jul 19
Total with taxes and fees
Luxe Mountain Home w/ Chef’s Kitchen & Okemo Views
House (5 Bedrooms) | Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
$1,679 nightly
The price is $1,847
Jul 18 - Jul 19
Total with taxes and fees
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Dining

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (17 reviews)
"Second time we have stayed here. Amazing home, amazing location. The flow and design makes us happy "
United States
karyn r.
$529 nightly
The price is $598
Jul 18 - Jul 19
Total with taxes and fees
New Ludlow Village Home with Stunning Okemo Mountain View
Exterior

Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
$211 nightly
The price is $239
Jul 20 - Jul 21
Total with taxes and fees
Cozy Studio Condo with Great Location, WiFi & Kitchenette
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Good location. Small pool and no chairs around pool"
Petra 2-night trip
Posted 23 hours ago
The Mountain Inn at Killington

Find out more about South Woodstock

Everything you need to know about South Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Woodstock vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Woodstock vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Woodstock. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $208 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Woodstock rentals

At Expedia, we put the best South Woodstock vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Woodstock vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: Visitors like this South Woodstock vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.