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Vacation rentals in Woodstock

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Quick stats about vacation rentals in Woodstock

  • Total vacation rentals

    Explore 20 vacation rentals in Woodstock

  • Nightly prices starting at

    Woodstock vacation rentals start at ﺩ.ﺇ 184 per night before taxes and fees

  • Verified guest reviews

    Over 1,980 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Woodstock vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woodstock rentals

  • 4.9 Average rating

    Woodstock stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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
4.96 out of 5 average rating, 444 reviews

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.

LocationFamilyCheckout

Top guest favorite
Cottage in Brimfield
4.98 out of 5 average rating, 99 reviews

Cheerful cottage by Little Alum Lake & Sturbridge

Little Alum is a gorgeous spring-fed lake in the quintessential New England town of Brimfield, MA. Brimfield is known as home to the largest flea market in the country. Little Alum is regarded as one of the cleanest lakes in Massachusetts due to its pristine water quality. The charming cottage is a one level home within close proximity to highways & downtown Sturbridge and off route 20 just a few minutes to downtown Brimfield and Antique show/flea market. Partial water views, steps to the water.

FamilyLocationQuiet

Top guest favorite
Cottage in Thompson
4.99 out of 5 average rating, 185 reviews

Peaceful Lakehouse | Thompson CT | Gorgeous Views

Escape to our beautifully renovated 1928 cottage on Quaddick Lake—your perfect retreat for relaxation and adventure. Just 60 minutes from Boston, Providence, and Hartford, this lakeside haven makes vacationing effortless. Start your day sipping coffee as the sunrise glows over the water and spend evenings by the crackling fire pit under the star filled sky. Whether paddling the lake or unwinding in cozy comfort, you'll feel miles away from the busy world, free to relax and make lasting memories.

ValueFamilyPets

Top guest favorite
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
5 out of 5 average rating, 260 reviews

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.

ValueFamilyKitchen

Top guest favorite
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.
Apartment in Woodstock
4.97 out of 5 average rating, 33 reviews

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!

FamilyLocationOutdoor spaces

Guest favorite
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.
Home in Woodstock
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.

LocationFamilyQuiet

Top guest favorite
Tiny home in Mansfield
5 out of 5 average rating, 29 reviews

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.

LocationCheck-inIndoor spaces

Guest favorite
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.
Home in Woodstock
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

FamilyLocationAmenities

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, 279 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.

FamilyLocationOutdoor spaces

Guest favorite
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
4.98 out of 5 average rating, 233 reviews

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.

LocationFamilyGetting around

Guest favorite
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.
Home in Woodstock
4.85 out of 5 average rating, 138 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! 🏡💖

FamilyValueCleanliness

Superhost
Home in Woodstock
4.71 out of 5 average rating, 14 reviews

Pool Side Cottage

Escape to this fully updated, professionally-designed poolside studio cottage featuring a full kitchen, bathroom, laundry, and cozy propane fireplace. Enjoy the attached pergola, outdoor kitchen, in-ground gunite pool, and exterior fireplace—perfect for romantic getaways or just a relaxing pool day. With beautiful indoor and outdoor spaces, this retreat is unforgettable. Ask about booking with the McClellan Mansion for even more space!

FamilyLocationComfort

Popular amenities for Woodstock vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Woodstock's top sights

Taylor Brooke Brewery

32 locals recommend

Roseland Cottage

26 locals recommend

Woodstock Orchards

16 locals recommend

Other great vacation rentals in Woodstock

Top guest favorite
Home in Woodstock
4.94 out of 5 average rating, 64 reviews

Country Lake Oasis

FamilyLocationBathroom

Guest favorite
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
4.91 out of 5 average rating, 74 reviews

The Maybrook: Lake & Sauna

FamilyLocationKitchen

Guest favorite
Guest suite in Woodstock
4.86 out of 5 average rating, 22 reviews

Woodstock Suite

LocationDecorCleanliness

Top guest favorite
Apartment in Woodstock
4.92 out of 5 average rating, 71 reviews

Woodstock Red Barn | Private Apt in Idyllic Town

FamilyLocationAir conditioning

Superhost
Home in Woodstock
4.63 out of 5 average rating, 8 reviews

Charming country village home.

LocationFamilyQuiet

Top guest favorite
A charming in-law suite stands in a serene setting, surrounded by open grassy fields. The house features a wraparound porch and carefully landscaped flower beds, framed by trees that provide a natural boundary. The driveway leads toward the entrance, welcoming visitors to a peaceful retreat.
Apartment in Thompson
4.99 out of 5 average rating, 74 reviews

Acoustical Haven: Unwind & Unplug

FamilyValueShared spaces

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
4.88 out of 5 average rating, 24 reviews

Charming Barn Loft with Modern Comforts

ValueLocationCheck-in

Superhost
An open kitchen and dining area features a high ceiling with exposed beams and two pendant lights. A small dining table with four black stools is positioned beside the window, while a stove and refrigerator are present against the black cabinetry.
Guesthouse in Thompson
4.83 out of 5 average rating, 53 reviews

Charming 2-Bedroom Barn Retreat on 20+ Acres

FamilyValueOutdoor spaces

Frequently Asked Questions

  • What are the best places to stay in Woodstock?

    Stays in Woodstock range from historic homes near the town green to countryside cottages surrounded by fields. Many accommodations have cozy communal living spaces and outdoor areas for relaxation.

  • What are the best things to do in Woodstock with kids?

    Plan a visit to local farms, seasonal festivals, and nature trails where children can explore and learn about the region’s history and environment. Hands-on activities and animal encounters are often featured at community venues.

  • What are some of the best things to do in Woodstock?

    Explore historic sites, nature preserves, and art galleries around Woodstock. The area frequently hosts farmers markets and craft fairs, making for engaging weekend experiences.

  • How is the weather in Woodstock?

    Woodstock experiences cold winters with temperatures from 17°F to 38°F (-8°C to 3°C) and milder, rainy springs. Summers are warm near 80°F (27°C), while autumn often brings crisp air and vibrant foliage.

  • When is the best time to visit Woodstock?

    Late spring through early autumn is often recommended for mild weather, colorful foliage, and a range of community events. Winter invites quieter experiences and views of snowy landscapes.

  • What are the best places to visit in Woodstock?

    Many visitors explore historic landmarks, serene lakes, and local galleries throughout Woodstock. The town has iconic meeting greens and traditional buildings that reflect its New England heritage.

  • What are some hiking trails in Woodstock?

    Woodstock has several scenic trails through woodland preserves and rural landscapes. Nature walks often feature birdwatching and wildflowers during warmer months.

  • What are some family activities we can do in Woodstock?

    Explore hands-on museums, enjoy seasonal outdoor festivals, or follow trails through community parks with the family. Farms around Woodstock often have activities for children, such as animal encounters and harvest-themed games.

  • What are some of the best day trip ideas from Woodstock?

    Explore nearby state parks, visit charming New England villages, or discover regional museums focused on local history and art. Outdoor activities and seasonal farm tours are also frequently suggested day excursions.

  • Are there any pet friendly accommodations available in Woodstock?

    Many accommodations in Woodstock welcome pets, especially in rural or countryside areas around the town. It’s helpful to check with hosts about specific amenities for traveling with your pet.

  • What are some local tips for visiting Woodstock?

    Layer up for changing weather, especially in spring and autumn. Exploring small shops and local trails around Woodstock can lead to unique finds, and many venues host seasonal community events.

  • What is Woodstock known for?

    Woodstock is known for its historic rural charm, traditional farmsteads, and community gatherings rooted in local culture. The area has scenic landscapes and often features art, music, and agricultural events.

  • What are the best hidden gems to explore in Woodstock?

    Seek out smaller art studios, quiet nature reserves, and historic cemeteries around Woodstock that provide insight into the area’s heritage. Community gardens and farm stands are also less-traveled spots to experience local character.

  • What are the best foods to try in Woodstock?

    Explore regional favorites such as locally made cheeses, fresh produce from area farms, and baked goods from community markets. Many cafes in Woodstock also highlight classic New England desserts and seasonal ingredients.

  • What should I bring for a trip to Woodstock?

    Bring comfortable shoes for exploring, clothing layers to accommodate temperatures from 17°F to 80°F (-8°C to 27°C), and a rain jacket for occasional showers. Binoculars and a camera help you get the most from outdoor excursions.

  • What is the nightlife in Woodstock like?

    Woodstock has a relaxed nightlife scene, centered on locally owned pubs, casual eateries, and occasional live music at community venues. Evenings tend to be calm and focused on conversation or small social gatherings.

  • What are the most popular events or festivals in Woodstock?

    Harvest fairs, holiday celebrations, and cultural festivals are frequently suggested in Woodstock, especially in late summer and autumn. Agricultural expositions are also common, celebrating the area’s farming traditions.

  • Are there family friendly vacation rentals in Woodstock?

    Family-friendly vacation rentals are available throughout Woodstock, ranging from countryside cottages to larger homes with communal spaces. Many have outdoor areas suitable for children to play and explore.

Destinations to explore