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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 G$10,459 GYD 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
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
5.0 out of 5 average rating, 261 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.

Top guest favorite
Cottage in Brimfield
4.98 out of 5 average rating, 104 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.

Guest favorite
A bright and inviting open-concept living area features two vibrant blue armchairs adorned with floral patterns. A wooden dining table is visible in the background, with a fully equipped kitchen displaying colorful cabinetry and modern appliances. Soft light enhances a welcoming atmosphere.
Home in Ashford
4.86 out of 5 average rating, 140 reviews

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

The Lake House, a two-story Designer's Dream, boasts scenic water and starry sky views. ● 397 Mbps Wi-Fi | 2x 55” Smart UHD TVs | Washer & Dryer | Indoor Fireplace ● Nintendo (NES) w/ 30 Games | Record Player w/ Vinyl Collection ● 3x Kayaks | 2x Stand Up Paddle Boards | 2x Cruiser Bikes | 2-Car Garage ● Gym (Bike, Yoga Mats, Weight Bands, Power Tower) ● Patio w/ Fire Pit & Grill| Full Kitchen | Coffee (Keurig) Drive to: ● UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

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, 35 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!

Top guest favorite
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
4.98 out of 5 average rating, 196 reviews

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!

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
4.95 out of 5 average rating, 77 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.

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

Woodstock Suite

Welcome to our cozy, private suite, thoughtfully designed for two guests! Nestled in the peaceful countryside of Woodstock, our newly built guest suite offers a quiet and comfortable getaway. We're also pet-friendly, so your furry companion is welcome! 🐾 Need a longer stay? We happily accommodate extended/multi-month reservations. Our suite is a great option for professionals, traveling workers, or those temporarily displaced by the foundation issues affecting homes throughout Eastern CT.

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, 277 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

Guest favorite
A feature wall is adorned with various steampunk elements, including gears, clocks, and unique decorative items. An intricately designed aircraft model is suspended from the ceiling, while a small table with a glass sits nearby, adding to the eclectic ambiance.
Farm stay in Thompson
4.94 out of 5 average rating, 263 reviews

SteamPunk Bunk House and Intergalactic Way Station

A farm stay like no other! The future is the past and the past is the future with STEAMPUNK details that delight at every turn. Feed the goats, walk the trails, meet an alien. A complete apartment great for longer stays. Enjoy the imagined history of this 1825 farm house. Enjoy New England without spending days driving. Come visit a simpler time where nature is just outside your door and ET is sharing the kitchen. Cook s'mores fireside or say hi to "blue" our resident heron.

Guest favorite
A inviting living area showcases a light gray couch and a blue accent chair, complemented by a decorative coffee table. A patterned area rug anchors the space, while a fireplace is adorned with seasonal decor and small evergreen trees, creating a cozy atmosphere.
Home in Southbridge
4.93 out of 5 average rating, 427 reviews

Charming Cape--Kid & Dog Friendly 🐾

Old style cape, newly renovated. Lots of vintage charm with new upgrades. Beautiful, 3 bedroom, 1.5 bath & full kitchen. Kitchen is fully stocked with duel kuereg and drip coffee pot & Ninja blender. Beautiful touches throughout to make your stay cozy. EXTRAS INCLUDE : 24-HOUR CHECK-IN / keyless entry FREE COFFEE HIGH SPEED WI-FI Pack N Play Glider for nursing/feeding moms! SMART TVs in 3 bedrooms Enjoy a cute stay in quiet neighborhood, 7 minutes from Sturbridge exit (84).

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, 282 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.

Top 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, 234 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.

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
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.
Apartment in Woodstock
4.98 out of 5 average rating, 97 reviews

Private apartment in a country home

Top guest favorite
Home in Woodstock
4.94 out of 5 average rating, 67 reviews

Country Lake Oasis

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, 54 reviews

Charming 2-Bedroom Barn Retreat on 20+ Acres

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

Charming country village home.

Guest favorite
A stone path winds through a lush green lawn, flanked by blooming pink rhododendron bushes. Two farmhouse-style buildings can be seen in the background, surrounded by trees, creating a serene and welcoming outdoor environment.
Farm stay in Southbridge
5.0 out of 5 average rating, 21 reviews

High Grass Farm

Top guest favorite
Tiny home in Mansfield
5.0 out of 5 average rating, 36 reviews

Handcrafted Timber Frame Cabin Retreat

Top guest favorite
A wide view of Alexanders Lake displays calm, blue waters surrounded by lush green and autumn-colored trees. The shoreline shows a mix of residential homes and natural areas, creating a serene and peaceful atmosphere. A clear blue sky complements the scenic landscape.
Home in Killingly
4.93 out of 5 average rating, 57 reviews

"The Getaway" at Alexanders Lake

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, 77 reviews

The Maybrook: Lake & Sauna

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