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

Guesthouse in Hartland

4.96 out of 5 average rating, 159 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.

Mar 13 – 20

G$32,979 GYD per night

Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 205 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.

Nov 6 – 13

G$32,970 GYD per night

Guest favorite

Cottage in Hartland

4.97 out of 5 average rating, 419 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!

Jan 1 – 8

G$25,653 GYD per night

Guest favorite

Barn in Woodstock

5.0 out of 5 average rating, 117 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.

Mar 19 – 26

G$126,642 GYD 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!

May 23 – 30

G$122,335 GYD per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 128 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

Jul 25 – Aug 1

G$24,858 GYD per night

Guest favorite

Barn in Woodstock

5.0 out of 5 average rating, 200 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.

Feb 15 – 22

G$67,318 GYD per night

Guest favorite

Tiny home in Hartland

4.94 out of 5 average rating, 252 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.

Jul 25 – Aug 1

G$27,471 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 491 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.

May 31 – Jun 7

G$20,773 GYD per night

Guest favorite

Cabin in Randolph

4.95 out of 5 average rating, 189 reviews

Secluded Log Home on 109 Acre Natural Wonderland!

Enjoy our remote, easily accessible, immaculate new log house, set in nature on 109 acres. Pond, woods, fields and trails; with high speed internet and smart TV! Sleeps 6, including a queen bed, 2 bunk beds, and a sleep sofa. Fully equipped kitchen, including a full-sized refrigerator, microwave, Keurig coffee maker and many other amenities. Screened in porch. Views from every room! In the heart of the ski corridor. Explore the trails, and the meditation yurt when available!

May 6 – 13

G$26,854 GYD per night

Guest favorite

Guest suite in Hartford

4.92 out of 5 average rating, 315 reviews

Sunny Side Airbnb (dog friendly)

Sunny Side Airbnb is located on a secluded 10+ acre property with plenty of outdoor space for dogs to run around and a short hiking trail with views. The Airbnb is located on the farther end of the house with garden views, a fire pit, and an open field. Convenient location near shops and restaurants. Just over a mile from I-89 off Rt 4 in Quechee, Vt. A short drive to WRJ and W Lebanon, NH, 9.1 miles to Woodstock, VT, 11 miles to Hanover, NH, and 13.4 miles to DHMC.

May 16 – 23

G$23,334 GYD per night

Guest favorite

Cabin in West Windsor

4.98 out of 5 average rating, 205 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 2 – 9

G$32,446 GYD 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

Home in Hartford

4.95 out of 5 average rating, 129 reviews

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Mar 24 – 31

G$132,415 GYD per night

Guest favorite

Tiny home in Hartland

4.95 out of 5 average rating, 144 reviews

Cabin on the Hill

Aug 25 – Sep 1

G$19,337 GYD per night

Guest favorite

Home in Bethel

4.84 out of 5 average rating, 127 reviews

Hike, run, swim or cycle in beautiful Central VT

Apr 15 – 22

G$24,850 GYD per night

Guest favorite

Cabin in Royalton

4.99 out of 5 average rating, 174 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Nov 14 – 21

G$32,362 GYD per night

Guest favorite

Cabin in Vershire

4.99 out of 5 average rating, 187 reviews

Comfortable cozy cabin in the hills of Vermont!

Jan 31 – Feb 7

G$23,998 GYD per night

Guest favorite

Tiny home in Woodstock

4.99 out of 5 average rating, 117 reviews

The Cluck House

Aug 23 – 30

G$32,383 GYD per night

Guest favorite

Cabin in Leicester

4.98 out of 5 average rating, 711 reviews

Log Cabin Getaway near Middlebury and Green Mtns

Dec 31 – Jan 7

G$26,300 GYD per night

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 585 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Nov 18 – 25

G$29,084 GYD per night

Show all

Other great vacation rentals in Woodstock

Guest favorite

Guesthouse in Putney

4.97 out of 5 average rating, 195 reviews

Cozy cottage loft and retreat

Nov 7 – 14

G$18,807 GYD per night

Guest favorite

Guest suite in Royalton

4.96 out of 5 average rating, 179 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

Jun 29 – Jul 6

G$25,026 GYD per night

Guest favorite

Tiny home in Pittsford

4.96 out of 5 average rating, 155 reviews

Charming tiny house with great VT location!

Jun 11 – 18

G$24,969 GYD per night

Guest favorite

Cabin in Grafton

4.9 out of 5 average rating, 114 reviews

“The Great Escape” Cabin - Pet Friendly!

Dec 6 – 13

G$19,537 GYD per night

Guest favorite

Home in Hartford

4.86 out of 5 average rating, 150 reviews

Beautiful Historic 1909 Library with a Fireplace

Jun 15 – 22

G$36,482 GYD per night

Guest favorite

Cabin in Bradford

4.98 out of 5 average rating, 331 reviews

Deer Valley Retreat, Lovely Log Cabin

Jan 2 – 9

G$30,566 GYD per night

Guest favorite

Cottage in Quechee

4.98 out of 5 average rating, 192 reviews

“The Maple Moose”, modern cabin near Woodstock

Aug 25 – Sep 1

G$55,185 GYD per night

Guest favorite

Home in Barnard

4.98 out of 5 average rating, 90 reviews

The Looking Glass, a modernistic escape

Jan 9 – 16

G$64,919 GYD 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	G$12,538 GYD 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 300 vacation rentals in Woodstock, over 10 vacation rentals in South Woodstock, and over 230 vacation rentals in Taftsville.
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 bed and breakfast rentals in Woodstock have wifi?
Absolutely! We offer over 30 bed and breakfast 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

Houses

Apartments

Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Other great vacation rentals in Woodstock

Home in Hartford

Tiny home in Hartland

Home in Bethel

Cabin in Royalton

Cabin in Vershire

Tiny home in Woodstock

Cabin in Leicester

Guesthouse in Wallingford

Other great vacation rentals in Woodstock

Guesthouse in Putney

Guest suite in Royalton

Tiny home in Pittsford

Cabin in Grafton

Home in Hartford

Cabin in Bradford

Cottage in Quechee

Home in Barnard

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 bed and breakfast 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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