South Woodstock Holiday Rentals

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Holiday Rentals in South Woodstock

Our top choices for South Woodstock holiday rentals

Stunning Lakefront Escape! Book Your Dream Getaway!

10.0 out of 10, Exceptional, (18)
"We had a great stay at the lakehouse. Will definitely consider a future stay."
The price is NZ$1,029
includes taxes & fees
8 Sept - 9 Sept
Stunning Lakefront Escape! Book Your Dream Getaway!

Dove Cabin up in the Trees

9.8 out of 10, Exceptional, (20)
"This is the sweetest property to stay in when visiting Brimfield market. I highly suggest any of the cabins on the property "
The price is NZ$437
includes taxes & fees
8 Sept - 9 Sept
Dove Cabin up in the Trees

The Tree House at Underhill Hollow

9.2 out of 10, Wonderful, (28)
"Great stay and the tree house was amazing. We loved walking the trails and finding all the fairy houses and interacting with the animals! "
The price is NZ$294
includes taxes & fees
8 Sept - 9 Sept
The Tree House at Underhill Hollow

Spacious Home Near Mohegan Sun

2.0 out of 10, (1)
"My stay at this rental was deeply unsettling and unsafe. The apartment itself has a creepy, neglected vibe, and it only got worst. A serious safety issue occured when a teenager in our group fell through a rotted, unstable deck/ a terrifying and completely preventable accident. Even more concerning, the entrance code to our apartment was the same code used for all other units in the building. This made me feel extremely unsafe as anyone from another unit could have accessed ours at any time....
The price is NZ$1,150
includes taxes & fees
15 Sept - 16 Sept
Spacious Home Near Mohegan Sun

Treehouse - Countryside - Farm Animals - Fire Pit

9.4 out of 10, Exceptional, (27)
"My husband and I were exploring a number of birding hotspots in the quiet corner and decided to try the treehouse. We woke to the dawn bird chorus (without any ambient road noise). Just dreamy!"
The price is NZ$492
includes taxes & fees
8 Sept - 9 Sept
Treehouse - Countryside - Farm Animals - Fire Pit

Brimfield Waterfront cottage

10.0 out of 10, Exceptional, (7)
"Property is in excellent condition, just the right amount of space for us. "
Brimfield Waterfront cottage

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

9.6 out of 10, Exceptional, (19)
"This lake house is a perfect, quiet & very pretty getaway! We absolutely loved our stay! The host was so sweet and easy to contact. We will be back!"
The price is NZ$554
includes taxes & fees
1 Oct - 2 Oct
Serene 2-bedroom, 2-bath lakefront retreat on scenic Staffordville Lake

Luxury Home, Pool, fireplace

10.0 out of 10, Exceptional, (29)
"A truly beautiful place with the most gorgeous pool and landscaping. We will be back for sure!"
Luxury Home, Pool, fireplace

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

9.4 out of 10, Exceptional, (15)
"Highly recommend for a peaceful location that offers everything you need to feel at home. "
The price is NZ$506
includes taxes & fees
10 Sept - 11 Sept
Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

Spacious 2 Bedroom 1 Bath apt

10.0 out of 10, Exceptional, (1)
"Great host and excellent apartment "
Spacious 2 Bedroom 1 Bath apt

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

9.8 out of 10, Exceptional, (111)
"The weather didn’t cooperate enough for us to enjoy the water, but it was lovely to look at"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Amazing lake house with everything you need!

9.8 out of 10, Exceptional, (16)
"Peaceful and safe for my family!Thank you Jason for this wonderful place."
Amazing lake house with everything you need!

4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

10.0 out of 10, Exceptional, (3)
"It was a pleasure staying here . The owner was always available. The house was updated and felt like home "
4-bedroom house in Windham - Pet Friendly - Thread City Family Escape

Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

10.0 out of 10, Exceptional, (56)
"This was a great and spacious property for our recent trip to the area for a family wedding. Everything was clean and as described with very responsive hosts!"
Beautiful Colonial Home in a Peaceful Setting Bordering Natchaug State Forest

Secluded 2-Acre Lakefront Home! Book Your Getaway!

9.8 out of 10, Exceptional, (72)
"We enjoyed our stay, especially sitting on the deck and listening to the birds. We would definitely love to return again sometime."
The price is NZ$865
includes taxes & fees
8 Sept - 9 Sept
Secluded 2-Acre Lakefront Home! Book Your Getaway!

Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'

10.0 out of 10, Exceptional, (49)
"We had a wonderful stay."
Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'

Wizard's Roost at Underhill Hollow

9.4 out of 10, Exceptional, (15)
"Full of whimsy, loved all of the details of the construction and decor. Great place to stay"
The price is NZ$266
includes taxes & fees
8 Sept - 9 Sept
Wizard's Roost at Underhill Hollow

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

9.0 out of 10, Wonderful, (21)
"We had such a wonderful time during our winter stay! The place was super cozy, and the heating made it feel like a warm retreat from the cold outside. We really appreciated the hospitality and can't wait to come back again! "
The price is NZ$558
includes taxes & fees
8 Sept - 9 Sept
Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

SteamPunk Bunk House and Intergalactic Way Station

10.0 out of 10, Exceptional, (9)
"This was a charming little apartment with a unique steam punk alien theme. If you have a playful mindset, I highly recommend staying at this location. I couldn’t have been more overjoyed with my stay."
The price is NZ$284
includes taxes & fees
8 Sept - 9 Sept
SteamPunk Bunk House and Intergalactic Way Station

Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!

10.0 out of 10, Exceptional, (3)
"Great little cottage at a lake. Super well appointed with pots, pans, gas grill, etc.... great hosts very attentive! "
Lakefront: Fish, Kayak, Canoe, Near Treehouse Brewery, Sturbridge Village!
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

Find out more about South Woodstock

Find out more about South Woodstock

Everything you need to know about South Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

South Woodstock holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Woodstock holiday rentals we have selected for you start as low as NZ$266 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on South Woodstock rentals

At Expedia, we put the best South Woodstock holiday 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 holiday.

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

Are there holiday rentals in South Woodstock?

Yes, there are holiday rentals close to the most popular sights in South Woodstock, or you can select a more secluded option if you're looking for a relaxing stay. South Woodstock is known for its golf courses and shopping.

What are some of the best holiday rentals that South Woodstock has to offer?

The Tree House at Underhill Hollow: This holiday home rental outside of South Woodstock offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a coffee maker and kitchenware.

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 holiday rental in South Woodstock like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Woodstock. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.