Woodstock vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Woodstock

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

Guest favorite

Guesthouse in Hartland

4.96 out of 5 average rating, 158 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 10 – 17

R2,988 ZAR per night
Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 203 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.

Jan 30 – Feb 6

R3,022 ZAR per night
Guest favorite

Cottage in Hartland

4.97 out of 5 average rating, 417 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!

Mar 17 – 24

R2,325 ZAR per night

Popular amenities for Woodstock vacation rentals

Stay near Woodstock's top sights

Billings Farm & Museum171 locals recommend
Woodstock Inn & Resort52 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

Tiny home in Warren

4.99 out of 5 average rating, 146 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Sep 1 – 8

R11,256 ZAR per night
Guest favorite

Home in Hartford

4.96 out of 5 average rating, 127 reviews

The Quechee Haus: VT Retreat with Outdoor Hot Tub

Apr 28 – May 5

R10,577 ZAR per night
Guest favorite

Tiny home in Woodstock

4.99 out of 5 average rating, 117 reviews

The Cluck House

Sep 5 – 12

R2,935 ZAR per night
Guest favorite

Barn in Fairlee

4.93 out of 5 average rating, 419 reviews

Private Barn On a Hilltop in Fairlee, Vermont

Dec 12 – 19

R2,912 ZAR per night
Guest favorite

Cabin in Groton

4.99 out of 5 average rating, 555 reviews

Peaceful Log Cabin in the Woods

Dec 14 – 21

R2,304 ZAR per night
Guest favorite

Cabin in Leicester

4.98 out of 5 average rating, 709 reviews

Log Cabin Getaway near Middlebury and Green Mtns

Jan 23 – 30

R2,383 ZAR per night
Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 581 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Jan 30 – Feb 6

R2,748 ZAR per night
Guest favorite

Apartment in Hartland

4.87 out of 5 average rating, 437 reviews

Sunny Studio Apartment in Hartland

Sep 9 – 16

R2,238 ZAR per night
Guest favorite

Tiny home in Hartland

4.95 out of 5 average rating, 144 reviews

Cabin on the Hill

Apr 29 – May 6

R1,752 ZAR per night
Guest favorite

Cabin in Vershire

4.99 out of 5 average rating, 185 reviews

Comfortable cozy cabin in the hills of Vermont!

Mar 12 – 19

R2,175 ZAR per night
Guest favorite

Cabin in Royalton

4.99 out of 5 average rating, 174 reviews

Genuine Vermont Sugar House on 70 peaceful acres.

Jan 2 – 9

R2,933 ZAR per night
Guest favorite

Guest suite in Royalton

4.95 out of 5 average rating, 174 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

Apr 10 – 17

R2,063 ZAR per night

Other great vacation rentals in Woodstock

Guest favorite

Apartment in Weathersfield

4.99 out of 5 average rating, 157 reviews

The Loft at Weathersfield

Oct 12 – 19

R2,322 ZAR per night
Guest favorite

Guesthouse in Putney

4.97 out of 5 average rating, 188 reviews

Cozy cottage loft and retreat

Nov 2 – 9

R1,704 ZAR per night
Guest favorite

Cottage in Bridgewater

4.96 out of 5 average rating, 139 reviews

Newly Renovated, Hot tub, 2min to Killington lift

Apr 23 – 30

R3,256 ZAR per night
Guest favorite

Cottage in Quechee

4.98 out of 5 average rating, 189 reviews

“The Maple Moose”, modern cabin near Woodstock

Aug 20 – 27

R5,001 ZAR per night
Guest favorite

Cabin in Bradford

4.98 out of 5 average rating, 328 reviews

Deer Valley Retreat, Lovely Log Cabin

Aug 11 – 18

R2,723 ZAR per night
Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Oct 4 – 11

R1,974 ZAR per night
Guest favorite

Apartment in Woodstock

4.94 out of 5 average rating, 102 reviews

Prospect Place

Feb 28 – Mar 7

R4,171 ZAR per night
Guest favorite

Chalet in Royalton

4.93 out of 5 average rating, 113 reviews

Scandinavian design Chalet w/ private hiking trail

Jan 24 – 31

R9,197 ZAR per night
Guest favorite

Apartment in Tunbridge

4.93 out of 5 average rating, 215 reviews

Fairview

Oct 17 – 24

R1,725 ZAR per night
Guest favorite

Farm stay in Plainfield

4.97 out of 5 average rating, 175 reviews

Renovated 1817 Hobby Farm Close to Dartmouth

Nov 25 – Dec 2

R2,826 ZAR per night
Guest favorite

Loft in Woodstock

4.98 out of 5 average rating, 173 reviews

The Loft at North House

Jan 31 – Feb 7

R2,414 ZAR per night
Guest favorite

Condo in Killington

4.92 out of 5 average rating, 143 reviews

Renovated, w/Covered Parking-Shuttle-Walk to Lifts

May 26 – Jun 2

R2,231 ZAR per night

Quick stats about vacation rentals in Woodstock

Total rentals

170 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

5.3K reviews

Nightly prices starting at

R1,704 ZAR 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 220 vacation rentals in Taftsville, over 10 vacation rentals in South Woodstock, and over 280 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 house rentals in Woodstock?

    Experience the best of Woodstock with our house rentals, starting at about $120 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 vacation rentals in Woodstock?

    Woodstock has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Woodstock