Woodstock vacation rentals

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Top-rated vacation rentals in Woodstock

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

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Guest favorite

Cabin in Royalton

4.99 out of 5 average rating, 174 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Feb 4 – 11

ﺩ.ﺇ569 per night

Guest favorite

Guesthouse in Hartland

4.96 out of 5 average rating, 160 reviews

Cottage for Two/Solo Getaway/Musician's Retreat

Luxurious, well appointed cottage with beautiful sunrise view located between Woodstock VT and Hanover NH. An inspiring treat for musician’s getaway is a fully restored 1929 Steinway L. Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer and very comfortable queen bed. A romantic getaway in the woods, a place to relax, work in peace, or explore the beauty and history of the area. Hiking, biking, fly fishing, hot air balloon rides and shopping are all close by.

Apr 2 – 9

ﺩ.ﺇ580 per night

Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 209 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.

Jul 15 – 22

ﺩ.ﺇ582 per night

Guest favorite

Cottage in Hartland

4.97 out of 5 average rating, 420 reviews

Breeze Hill Cottage

This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!

Apr 8 – 15

ﺩ.ﺇ451 per night

Guest favorite

Barn in Woodstock

5.0 out of 5 average rating, 119 reviews

Stunning Converted Barn Home 3-bed 2 bath

Stunning renovated barn, surrounded by fenced pastures, this beautiful authentic barn home provides guests with a unique experience, in a beautiful 3-bedroom, 2 bath rustic barn. Fully equipped, beautifully decorated with high end furnishings, antique rugs, comfortable beds, cook in the chef's kitchen, relax by the stone fireplace, sit on the deck with amazing views, walk the fields, and enjoy thethe fireplace pit. An original classic barn, you won't forget. Srry we can no longer accept pets.

Apr 16 – 23

ﺩ.ﺇ2,014 per night

Guest favorite

Home in Woodstock

5.0 out of 5 average rating, 110 reviews

Beautiful Woodstock Home-Perfect for entertaining

Newly renovated - 4 bedroom, 3 bath house, perfect for relaxing or entertaining. Close to all that the Woodstock Village and the Upper Valley has to offer. Amazing location! Only 1.5 mi to the Woodstock Green. Explore the property and feast on the blackberries in summer, raid the tomato garden in the late summer/early fall, and pick the wild fall apples for munching or baking. Bring your snowshoes or cross country skis (in winter) or hiking shoes in summer and explore the property and beyond!

Sep 17 – 24

ﺩ.ﺇ2,217 per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 131 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

Sep 3 – 10

ﺩ.ﺇ366 per night

Guest favorite

Barn in Woodstock

5.0 out of 5 average rating, 201 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". The loft is a newly built apartment on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a Cathedraled living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony.

Dec 27 – Jan 3

ﺩ.ﺇ1,183 per night

Guest favorite

Tiny home in Hartland

4.94 out of 5 average rating, 253 reviews

Private Modern Cabin w/View of Fields, Hills

Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $29 pet fee applies.

Nov 7 – 14

ﺩ.ﺇ483 per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 495 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Sep 18 – 25

ﺩ.ﺇ375 per night

Guest favorite

Cabin in West Windsor

4.98 out of 5 average rating, 206 reviews

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just a few minutes from Mt. Ascutney's hiking and mountain-biking trails and in the middle of fantastic cycling country. WiFi now available! Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring Vermont.

Jul 27 – Aug 3

ﺩ.ﺇ570 per night

Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 394 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Mar 19 – 26

ﺩ.ﺇ512 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Woodstock vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Woodstock's top sights

Woodstock Inn & Resort52 locals recommend

Billings Farm & Museum171 locals recommend

Worthy Kitchen110 locals recommend

Woodstock Farmers' Market92 locals recommend

Marsh - Billings - Rockefeller National Historical Park43 locals recommend

Mon Vert Cafe44 locals recommend

Other great vacation rentals in Woodstock

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 590 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Apr 12 – 19

ﺩ.ﺇ495 per night

Guest favorite

Guest suite in Hartford

4.91 out of 5 average rating, 318 reviews

Sunny Side Airbnb (dog friendly)

Jun 22 – 27

ﺩ.ﺇ478 per night

Guest favorite

Cabin in Vershire

4.99 out of 5 average rating, 189 reviews

Comfortable cozy cabin in the hills of Vermont!

Apr 7 – 14

ﺩ.ﺇ422 per night

Guest favorite

Tiny home in Hartland

4.95 out of 5 average rating, 146 reviews

Cabin on the Hill

Sep 7 – 14

ﺩ.ﺇ340 per night

Guest favorite

Cabin in Leicester

4.98 out of 5 average rating, 713 reviews

Log Cabin Getaway near Middlebury and Green Mtns

Apr 25 – May 2

ﺩ.ﺇ462 per night

Guest favorite

Tiny home in Woodstock

4.99 out of 5 average rating, 117 reviews

The Cluck House

Mar 6 – 13

ﺩ.ﺇ569 per night

Guest favorite

Tiny home in Warren

4.99 out of 5 average rating, 154 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Aug 13 – 20

ﺩ.ﺇ2,055 per night

Guest favorite

Guesthouse in Putney

4.97 out of 5 average rating, 199 reviews

Cozy cottage loft and retreat

Feb 27 – Mar 6

ﺩ.ﺇ331 per night

Show all

Other great vacation rentals in Woodstock

Guest favorite

Home in Hartford

4.95 out of 5 average rating, 130 reviews

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Nov 10 – 17

ﺩ.ﺇ2,349 per night

Guest favorite

Guest suite in Brownsville/West Windsor

4.99 out of 5 average rating, 161 reviews

Cozy Guest Suite in Charming Farmhouse

May 27 – Jun 3

ﺩ.ﺇ599 per night

Guest favorite

Guest suite in Royalton

4.96 out of 5 average rating, 167 reviews

Bluestone Farm

Jul 24 – 31

ﺩ.ﺇ430 per night

Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Nov 5 – 12

ﺩ.ﺇ376 per night

Guest favorite

Cabin in Randolph

4.95 out of 5 average rating, 193 reviews

Secluded Log Home on 109 Acre Natural Wonderland!

Aug 23 – 30

ﺩ.ﺇ578 per night

Guest favorite

Farm stay in Plainfield

4.97 out of 5 average rating, 176 reviews

Renovated 1817 Hobby Farm Close to Dartmouth

Nov 24 – Dec 1

ﺩ.ﺇ548 per night

Guest favorite

Cabin in Bradford

4.98 out of 5 average rating, 333 reviews

Deer Valley Retreat, Lovely Log Cabin

Nov 4 – 11

ﺩ.ﺇ526 per night

Guest favorite

Cabin in Grafton

4.91 out of 5 average rating, 116 reviews

“The Great Escape” Cabin - Pet Friendly!

Oct 25 – Nov 1

ﺩ.ﺇ340 per night

Show all

Quick stats about vacation rentals in Woodstock

Total rentals
180 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
5.6K reviews
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees

Frequently Asked Questions

Where should I stay in Woodstock?
Make yourself at home in Woodstock by choosing from our most frequently booked neighborhoods. We have over 230 vacation rentals in Taftsville, over 10 vacation rentals in South Woodstock, and over 300 vacation rentals in Woodstock.
Are there vacation rentals with a dedicated workspace in Woodstock?
Yes! Work meets play with ease at over 70 vacation rentals in Woodstock featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Woodstock?
Four-legged friends are welcome in Woodstock. Choose from more than 60 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Woodstock?
Experience the best of Woodstock with our apartment rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Woodstock have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodstock have wifi?
Absolutely! We offer over 50 house rentals with wifi in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Woodstock have self check-in?
Absolutely! We offer over 20 house rentals with self check-in in Woodstock. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Woodstock?
Woodstock has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Woodstock vacation rentals

Top-rated vacation rentals in Woodstock

Vacation rentals for every style

Cabins

Apartments

Houses

Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Other great vacation rentals in Woodstock

Guesthouse in Wallingford

Guest suite in Hartford

Cabin in Vershire

Tiny home in Hartland

Cabin in Leicester

Tiny home in Woodstock

Tiny home in Warren

Guesthouse in Putney

Other great vacation rentals in Woodstock

Home in Hartford

Guest suite in Brownsville/West Windsor

Guest suite in Royalton

Cabin in Londonderry

Cabin in Randolph

Farm stay in Plainfield

Cabin in Bradford

Cabin in Grafton

Quick stats about vacation rentals in Woodstock

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Where should I stay in Woodstock?

Are there vacation rentals with a dedicated workspace in Woodstock?

Are there pet-friendly vacation rentals in Woodstock?

How much does it cost to stay in apartment rentals in Woodstock?

Do house rentals in Woodstock have a bbq area?

Do house rentals in Woodstock have wifi?

Do house rentals in Woodstock have self check-in?

Are there family-friendly house rentals in Woodstock?

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