Holiday houses in Woodstock

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Top-rated holiday rentals in Woodstock

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Guest favourite

Apartment in Woodstock Valley

4.93 out of 5 average rating, 335 reviews

“Tranquillity on the Lake ” Woodstock Valley, Ct.

Spring into the warm weather of April and May. Enjoy the beautiful view from your private lakeside suite. 1,400 sq feet of living space. Featuring Queen bed in Master. Queen sofa in living area. Cozy indoor propane fireplace. Kitchen stove, full refrigerator, microwave. Enjoy private deck, propane fire pit, gaze at the moon & stars. Cook-Propane grill. Enjoy scenic walks around the lakes. Wake up to amazing sunrises. Pretty flowers, trees surrounding!! Woodstock Valley Country within two miles!

22 – 29 Apr

$1,731 AUD total

Guest favourite

Farm stay in Southbridge

4.98 out of 5 average rating, 163 reviews

High Grass Farm

Get cozy in front of the fireplace and enjoy a romantic getaway in our beautiful and historic old house. One of the top 16 farm stays in New England! Our 1780's farmhouse has been completely renovated and retains its rustic country feel. Experience early American period life with only a few modern conveniences (e.g. full laundry and 5G wi-fi). Our secluded setting on 19 acres in southern Mass is minutes from I-90 and I-84, and borders CT, Old Sturbridge Village and the Westville recreation area.

1 – 8 Nov

$2,248 AUD total

Guest favourite

Treehouse in Thompson

4.96 out of 5 average rating, 331 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.

1 – 8 July

$1,706 AUD total

Guest favourite

Guest suite in Thompson

4.98 out of 5 average rating, 114 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!

23 – 30 Aug

$1,831 AUD total

Guest favourite

Guest suite in Warren

4.95 out of 5 average rating, 265 reviews

Craig's Cove

Craig's Cove is a two-room apartment (in my finished basement) with a farmhouse industrial motif and is in close proximity to Sturbridge, wineries, micro-brews such as Lost Towns Brewing, and beautiful scenery. Guests will be provided with one off-street parking space, private entry, bedroom with queen-size bed, full bathroom, TV with Netflix & Amazon Prime, free wifi, coffee, kitchenette with sink, microwave, fridge, toaster oven, hot plate (no full size stove), and patio with pergola.

16 – 23 Sept

$839 AUD total

Guest favourite

Farm stay in Thompson

4.99 out of 5 average rating, 133 reviews

Rustic Farmette Studio w/ Hot Tub & seasonal pool

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, a small family. Please include all individuals (&pets) in your booking.

22 – 29 July

$2,507 AUD total

Guest favourite

Home in Woodstock

4.93 out of 5 average rating, 207 reviews

Cedar Ridge

In Connecticut's "Quiet Corner", a fully renovated 2-level house bathed in sunlight, with lovely flower beds and stunning hilltop views. Relax on its patios and in its small swimming pool, stroll along its forest paths, observe birds (including birds of prey) and other wildlife. New England's "Last Green Valley National Heritage Corridor" offers multiple attractions and is home to many schools, universities, fairs, artists/artisans, farms, special events and year-round activities.

30 Dec – 6 Jan

$3,731 AUD total

Guest favourite

Apartment in Brimfield

4.98 out of 5 average rating, 138 reviews

Quiet & Cozy Main Street Retreat

Skip the traffic on the way to popular seasonal tourist destination, the Brimfield Flea Market, by staying here the night prior to your visit! Or, complement an off-season stay with an abundance of hiking trails, antique shops, lakes, farms, and even a winery just a 5 minute walk from your doorstep. Enjoy the convenience of a convenience store, package store, and post office across the way, combined with the peace and quiet of this private suite tucked behind the main house.

21 – 28 Dec

$1,618 AUD total

Guest favourite

Farm stay in Woodstock

4.98 out of 5 average rating, 168 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.

23 – 30 Nov

$1,801 AUD total

Superhost

Home in Woodstock

4.92 out of 5 average rating, 133 reviews

Lakeside Paradise — HotTub, Kayaks, & Bonus Cabin

In CT's tranquil and majestic "Quiet Corner" this private 4-acre estate located on Lake Chamberlain comes replete with your very own cove. Known for its bass fishing and beautiful birds, the lake is wonderful for swimming, kayaking, and reveling in nature. The 4-bedroom home has a modern farmhouse interior and bespoke design finishes throughout. Outdoor amenities include a hot tub, fire pit area, BBQ, kayaks, dock, lawn games, and a massive deck.

12 – 19 Sept

$7,259 AUD total

Guest favourite

Apartment in Ashford

4.97 out of 5 average rating, 144 reviews

On The Run Farm

Quiet country setting, minutes from UCONN and easy access from RTE 84 makes this place perfect for visitors traveling through the "Quiet Corner" of CT. Spacious living room, bedroom. kitchen and bath are newly renovated with, hardwood floors, skylights, and windows that allow for lots of natural light. The entryway is private with a lovely porch that is a great place to sit with your morning coffee. Hiking trails can be accessed from the property.

21 – 28 Nov

$1,614 AUD total

Superhost

Cottage in Chaplin

4.88 out of 5 average rating, 128 reviews

Clark Cottage in the historic village in Chaplin

Up to 14 day stays are OK. Cottage is empty several days between guests. Virus cleaning protocol in use. This little rustic cottage, circa 1850, has antique charm, yet modern comforts. In addition to a living and dining room, there is a full vintage kitchen, 2 bedrooms, 1 bathroom, plus laundry facilities. Very tall people will have to duck under door ways. Not suitable for children under 12. WiFi and a smart TV. Kitchen ceiling is 6'3.5".

3 – 10 Nov

$1,728 AUD total