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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

Terrace/patio

Stunning Lakefront Escape! Book Your Dream Getaway!

Stunning Lakefront Escape! Book Your Dream Getaway!
Woodstock
10.0 out of 10, Exceptional, (26 reviews)
"Great experience. Thank you "
United States
edmund d.
$652 nightly
The price is $738
Jul 20 - Jul 21
Total with taxes and fees
Stunning Lakefront Escape! Book Your Dream Getaway!
Interior

The Tree House at Underhill Hollow

The Tree House at Underhill Hollow
Thompson
9.4 out of 10, Exceptional, (39 reviews)
"Nice place to stay has good air conditioning "
United States
Zachary P.
$171 nightly
The price is $194
Jul 21 - Jul 22
Total with taxes and fees
The Tree House at Underhill Hollow
Exterior

Wizard's Roost at Underhill Hollow

Wizard's Roost at Underhill Hollow
North Grosvenordale
9.6 out of 10, Exceptional, (23 reviews)
"I stayed here for the 2026 Natchaug Epic gravel bike ride, and it was an ideal location, close to the start line. A charming property with a friendly host. "
United States
Mateo A.
$166 nightly
The price is $188
Jul 22 - Jul 23
Total with taxes and fees
Wizard's Roost at Underhill Hollow
Exterior

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor

Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Putnam
8.8 out of 10, Excellent, (5 reviews)
"Clean place, easy check-in and comfortable place. We appreciated the coffee and water, microwave and clean towels. We would stay here again!! Thank you!! "
United States
Lucy L.
$225 nightly
The price is $255
Jul 21 - Jul 22
Total with taxes and fees
Charming 2-bedroom apartment in welcoming Putnam - 2nd Floor
Property grounds

SteamPunk Bunk House and Intergalactic Way Station

SteamPunk Bunk House and Intergalactic Way Station
Thompson
10.0 out of 10, Exceptional, (16 reviews)
"Enjoyed our stay. Loved being out in the countryside "
United States
Pauline S.
$181 nightly
The price is $205
Aug 2 - Aug 3
Total with taxes and fees
SteamPunk Bunk House and Intergalactic Way Station
Exterior

The Carriage House at Chaprae Hall

The Carriage House at Chaprae Hall
Killingly
10.0 out of 10, Exceptional, (33 reviews)
"Just as advertised clean and comfortable, thank you gentlemen. Keep up the good work. :)"
United States
Herbert
$186 nightly
The price is $211
Aug 17 - Aug 18
Total with taxes and fees
The Carriage House at Chaprae Hall
Exterior detail

Cozy 1-bedroom cottage in serene Pomfret.

Cozy 1-bedroom cottage in serene Pomfret.
Pomfret
10.0 out of 10, Exceptional, (1 review)
"We were up in Pomfret for a wedding in the area. Perfect location for us; walkable to a local cafe (Vanilla Bean) for breakfast. The place sits on a large piece of property complete with pond; beautiful setting, very peaceful. Plenty of space for parking; water pressure was great for showers and appreciate the travel size lotions, shampoo, etc ! Overall a great experience. Would highly recommend, especially for parents of students who attend The Pomfret School (boarding). Perfect location...
United States
Stephanie K.
$277 nightly
The price is $314
Jul 20 - Jul 21
Total with taxes and fees
Cozy 1-bedroom cottage in serene Pomfret.
Property grounds

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing

Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Willington
9.8 out of 10, Exceptional, (16 reviews)
"We loved the ambience, super quiet, my kids love the animals The host was super comunicative making sure we was good during our stay"
United States
Silvino
$204 nightly
The price is $231
Aug 3 - Aug 4
Total with taxes and fees
Farm - Animals - Barn - Gazebo - Fire Pit - 2xKing
Interior

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge

Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Sturbridge
$117 nightly
The price is $131
Jul 20 - Jul 21
Total with taxes and fees
Charming 1-bedroom apartment with AC & Breakfast in Sturbridge
Exterior

Treehouse - Countryside - Farm Animals - Fire Pit

Treehouse - Countryside - Farm Animals - Fire Pit
Willington
9.4 out of 10, Exceptional, (34 reviews)
"The tree house matched the description perfectly! The host was very responsive, the house was clean, and the temperature was comfortable. All instructions were provided prior to our arrival and easy to understand. The manager was friendly and we loved spending time with the animals. It was a little pricey but I would stay again. Great getaway for my husband and i to connect with nature!"
United States
Pattie
$265 nightly
The price is $300
Aug 5 - Aug 6
Total with taxes and fees
Treehouse - Countryside - Farm Animals - Fire Pit
Interior

Spacious, unique barn with beautiful views.

Spacious, unique barn with beautiful views.
Hampton
9.6 out of 10, Exceptional, (4 reviews)
"I was looking for a place that was central to a couple of Renaissance Faires in the area and ended uo choosing this one due to its location and affordability. What an awesome place to stay. We're considering staying here next year when the Faires return."
United States
Kevan W.
$234 nightly
The price is $264
Jul 21 - Jul 22
Total with taxes and fees
Spacious, unique barn with beautiful views.
Exterior

Dove Cabin up in the Trees

Dove Cabin up in the Trees
Holland
9.8 out of 10, Exceptional, (31 reviews)
"So calm, clean and relaxing, and beautiful! Wonderful stay! "
United States
Sarah G.
$244 nightly
The price is $257
Jul 20 - Jul 21
Total with taxes and fees
Dove Cabin up in the Trees
Outdoor dining

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Ashford
9.6 out of 10, Exceptional, (22 reviews)
"The location of the home was perfect. The lake was beautiful and was a great place to walk. "
United States
Lynn D.
$384 nightly
The price is $435
Aug 18 - Aug 19
Total with taxes and fees
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
Terrace/patio

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
Stafford
9.6 out of 10, Exceptional, (45 reviews)
"What a relaxing cottage! "
United States
Dana B.
$310 nightly
The price is $351
Jul 30 - Jul 31
Total with taxes and fees
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake
TV

6 Beds Home w/Game Room Perfect for Groups

6 Beds Home w/Game Room Perfect for Groups
Killingly
$588 nightly
The price is $698
Jul 20 - Jul 21
Total with taxes and fees
6 Beds Home w/Game Room Perfect for Groups
Smart TV

Serenity meets Taradise

Serenity meets Taradise
Union
$153 nightly
The price is $173
Jul 27 - Jul 28
Total with taxes and fees
Serenity meets Taradise
Exterior

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Ashford
9.2 out of 10, Wonderful, (36 reviews)
"Adorable cottage in a great location with all the items we needed to enjoy our time. "
United States
Lynn R.
$437 nightly
The price is $495
Jul 26 - Jul 27
Total with taxes and fees
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak
Property grounds

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony

Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Webster
9.6 out of 10, Exceptional, (5 reviews)
"Owner was easy to communicate with. Cute and cozy unit that meet all of our needs for our trip."
United States
Rachele T.
$339 nightly
The price is $379
Jul 26 - Jul 27
Total with taxes and fees
Family-friendly 2- Bedroom Webster Home w/Cozy Balcony
Dining

Secluded 2-Acre Lakefront Home! Book Your Getaway!

Secluded 2-Acre Lakefront Home! Book Your Getaway!
Woodstock
9.8 out of 10, Exceptional, (87 reviews)
"The hosts were welcoming and the house was very clean and a great place to stay!"
United States
Emma S.
$681 nightly
The price is $771
Jul 20 - Jul 21
Total with taxes and fees
Secluded 2-Acre Lakefront Home! Book Your Getaway!
Interior

Cozy Chic Countryside Haven - Sleeps 4 , Firepit

Cozy Chic Countryside Haven - Sleeps 4 , Firepit
Sturbridge
10.0 out of 10, Exceptional, (2 reviews)
"The place was immaculate, very large room, great kitchen, great bath, plenty of room for a family, quiet and secluded area few minutes away from town, outstanding communication with the property owner..true home away from home...Try it for yourself.."
United States
Giora Y.
$319 nightly
The price is $356
Jul 30 - Jul 31
Total with taxes and fees
Cozy Chic Countryside Haven - Sleeps 4 , Firepit
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

Wellsworth Hotel

Wellsworth Hotel

10/10 Excellent
"Quiet clean place."
diane 1-night trip
Posted 2 hours ago
Wellsworth Hotel

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 $96 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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in South Woodstock?

Yes, you can find vacation rentals near top sights in South Woodstock, or you can go with a more remote option if you're looking for relaxation. South Woodstock is known for its golf courses and shopping.

What are some of the best vacation home rentals in South Woodstock?

Stunning Lakefront Escape! Book Your Dream Getaway!: Visitors give good reviews to this South Woodstock vacation home rental, which is located on the beach and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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

Explore the area and family-friendly sights such as TriState Speedway, or get out into nature at a spot like Walker Dam. Little River Plaza Shopping Center and Harrisville Golf Course are other places to visit while you're in town.

What’s a vacation rental in South Woodstock like?

Vacation rentals are privately owned properties you can stay in for a long or short time in South Woodstock. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for small groups.