Holiday rentals in Woodstock

4.96 out of 5 average rating, 437 reviews

A colorful treehouse stands elevated among the trees, featuring a wooden deck with railings. The exterior showcases a playful combination of purple, yellow, and red, with multiple windows inviting natural light. The surrounding foliage adds to the charming, secluded atmosphere.

Treehouse in Thompson

The Tree House at Underhill Hollow

The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.

5.0 out of 5 average rating, 257 reviews

The exterior of a rustic wooden house is surrounded by lush greenery and trees. A small fenced area is visible near the entrance, where a welcoming front door can be seen. The building features windows and a gabled roof, set in a tranquil natural environment.

Farm stay in Thompson

Rustic Farmette Studio w/yearround Hot Tub

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

4.97 out of 5 average rating, 30 reviews

A spacious studio apartment features a queen bed with a light-colored coverlet. A cozy seating area includes a sofa and a colorful patterned chair next to a small table. Bright light from a floor lamp highlights the room, while a ceiling fan adds comfort.

Flat in Woodstock

Quiet Corner Studio

Kick back and relax in our calm,stylish space.This studio apt features a separate entrance in back of garage.A staircase leads up to a deck with a table and chairs for outdoor dining and relaxing.Catch a glimpse of our Highland cows peacefully grazing the day away.This studio apt is cozy,thoughtfully decorated, and stocked with all your necessities.Queen bed,Full size refrigerator, stove/oven, kuerig,toaster,microwave.Linens,blankets,pillows,throw pillows,towels.Your home away from home awaits!

4.93 out of 5 average rating, 60 reviews

Country Lake Oasis

Escape to tranquility at this waterfront retreat! Breathtaking sunset views over a pristine, swimmable lake with a sandy beach and floating dock. Newly updated home features a relaxing spacious deck, fully equipped kitchen and pristine wood floors. Nestled on a quiet dead-end street, this haven offers a kayak and paddle boat for water adventures. Embrace the serenity with an outdoor fire pit, fishing from the pier, and lakeside BBQs. Inside, discover an Experience rural beauty. Paradise awaits!

4.98 out of 5 average rating, 191 reviews

A single-story farmhouse features a covered front porch adorned with hanging plants. A well-maintained lawn surrounds the home, complemented by landscaped bushes. An American flag is displayed, and tall trees line the background, providing a natural setting.

Guest suite in Thompson

Meadowside: Perfect Location w/ Endless Recreation

Perfect location, great value, & tons of privacy! Come stay at Meadowside! You'll be in a beautifully appointed and completely private 620 sq ft in-law suite. We're a quarter mile away from Webster Lake and an easy drive to all area attractions! Bring your boat, as we have plenty of room for your trailer in our parking lot-sized driveway! Room to sleep up to 4, king bed in the master, 1.5 baths, kitchen, laundry, front farmer's porch, and garden dining! You name it, it's here at Meadowside!

A mid-century modern cabin is set against a backdrop of vibrant autumn foliage. The structure features large windows and a spacious deck facing the tranquil lake. Lounge chairs are arranged along the water's edge, inviting relaxation amid the colorful trees.

4.96 out of 5 average rating, 74 reviews

Mid-Century Modern Lakefront Cabin

Welcome to our 1966 Scandinavian mid-century modern cabin in the woods . Renovated with every modern amenity, and lake views out every window. With direct lake access & shallow waters, it’s great for families with young children. Perfect for wedding party prep & lakefront photos! In "The Quiet Corner" near UCONN, Eastern, Woodstock/Pomfret Academies, Clark + Trinity, wine trail, hiking, antiques & farm stands. Our place isn’t for big parties. It’s quiet & geared toward family & friends.

5.0 out of 5 average rating, 21 reviews

Tiny home in Mansfield

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

The renovated house is situated amidst lush greenery, surrounded by trees and a well-maintained lawn. A small swimming pool is visible within a fenced area, complemented by several umbrellas for shade, enhancing the outdoor ambiance on a sunny day.

4.92 out of 5 average rating, 273 reviews

Cedar Ridge: House

HOUSE in CT’s Quiet Corner: Renovated house bathed in light, with nice stunning hilltop views. Relax on its patios and small swimming pool, stroll along its forest paths, Located in New England's "Last Green Valley National Heritage Corridor" offers multiple attractions, home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities. NOTE: RENTED DOWNSTAIRS APARTMENT. OWN PRIVATE ENTRANCE. DOES NOT SHARE OUTDOOR SPACE, PATIO, OR POOL

4.98 out of 5 average rating, 199 reviews

A comfortable living area is furnished with a light brown sofa and two accent chairs. Artwork is displayed on the wall, and a coffee table sits atop a patterned area rug. Natural light enters through the windows, illuminating the cozy space.

Guest house in Killingly

The Carriage House at Chaprae Hall

Welcome to the Carriage House at Chaprae Hall! A cozy, quiet respite from a busy world awaits you. This fully furnished & appointed vintage living space has been updated over the years to be an inviting and welcoming stop for your journey. Whether you’re traveling for business, in town for an event, or looking for a central home base for day trips across southern New England, we've got you covered with your own kitchen, full bath, living space, and bedroom with a queen-sized bed.

Superhost

A living room is displayed with hardwood flooring and a circular braided rug. Furnishings include a sofa and two high-backed chairs near a large window that offers views of greenery. A coffee table is positioned centrally, with a faux fireplace and a television visible in the background.

Home in Putnam

4.78 out of 5 average rating, 275 reviews

Calm & Cozy House in a Quiet Corner

The perfect place to get away to enjoy a Best Kept Secret of New England. You will have access to the whole house during your stay. All on one level (ground floor). Enjoy the relaxing view of the field, red barn and Quinnebaug River while snuggling up with read a book. The country kitchen is complete with refrigerator, toaster, oven, microwave, and coffee maker. The best of Putnam Antique District, Entertainment, Dining, Nightlife and shopping a 4 minute drive away.

4.98 out of 5 average rating, 229 reviews

The exterior of a red, two-story building is surrounded by a well-maintained lawn featuring trees and landscaped flower beds. A large window above the entrance and additional windows enhance the farmhouse aesthetic. Cloudy skies and natural light create a serene atmosphere.

Farm stay in Woodstock

Barn suite at Southwood Alpacas

Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.

The exterior of a charming green house is framed by vibrant flowering shrubs and manicured lawn. A prominent brick chimney rises from the roof, surrounded by lush greenery that enhances the home's inviting presence.

4.85 out of 5 average rating, 137 reviews

Secluded 2 Acre Lake Front Home!

Escape to this breathtaking retreat on Lake Chamberlain, tucked away in Connecticut's serene "Quiet Corner". This spacious 2-acre home offers total privacy and stunning natural beauty. In the summer, dive into swimming, fishing, and kayaking 🛶🏊‍♀️. When winter arrives, experience ice skating ⛸️ right on the lake! Whether you're here for relaxation or adventure, this peaceful getaway will steal your heart. Once you arrive, you may never want to leave! 🏡💖

Popular amenities for Woodstock holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Woodstock

4.98 out of 5 average rating, 96 reviews

A large, welcoming home is surrounded by vibrant autumn foliage. The house features a well-kept lawn and a front porch, providing a charming view of the colorful trees in the background, under a clear blue sky.

Flat in Woodstock

Private apartment in a country home

5.0 out of 5 average rating, 6 reviews

Charming country village home.

4.9 out of 5 average rating, 73 reviews

A charming blue cottage is set amidst colorful autumn foliage. The front features a well-maintained garden with ornamental flowers and a stone pathway leading to the entrance. A small seating area with chairs invites relaxation, complemented by a wooden railing along the deck.

Cottage in Holland

The Maybrook: Lake & Sauna

5.0 out of 5 average rating, 78 reviews

The cottage blends into the natural landscape, framed by vibrant fall foliage. The structure features large windows and a gable roof, while greenery surrounds the entrance, creating an inviting view of the serene outdoor environment.

Guest house in Pomfret

Cottage in Quiet Corner. Four miles from town.

4.91 out of 5 average rating, 68 reviews

Flat in Woodstock

Woodstock Red Barn | Private Apt in Idyllic Town

5.0 out of 5 average rating, 62 reviews

The exterior of a spacious barn structure is visible against a clear blue sky. The building features a gabled roof and light-colored wooden siding. Large double doors are positioned at the front, with a smaller door on the side. Leafless trees surround the barn.

Barn in Hampton

Little Rest Studio

Superhost

The spacious barn loft features a wooden floor and a high ceiling, accented by wooden paneling on the walls. A cozy bed is paired with a lounge area containing a sofa. A staircase leads to an upper loft space, with modern lighting fixtures visible above.

Barn in Thompson

4.85 out of 5 average rating, 20 reviews

Charming Barn Loft with Modern Comforts