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
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.
Sep 24 – Oct 1
ﺩ.ﺇ498 per night
4.96 out of 5 average rating, 158 reviews
Guest favorite
Guesthouse in Woodstock
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.
Jun 3 – 10
ﺩ.ﺇ506 per night
4.98 out of 5 average rating, 203 reviews
Guest favorite
Cottage in Hartland
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!
Feb 11 – 18
ﺩ.ﺇ390 per night
4.97 out of 5 average rating, 418 reviews

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 Hartland
Private Modern Cabin w/View of Fields, Hills
Dec 10 – 17
ﺩ.ﺇ421 per night
4.94 out of 5 average rating, 251 reviews
Guest favorite
Condo in Killington
🎿Cozy Fireplace Condo-Mins. to Everything 🚵
Apr 30 – May 7
ﺩ.ﺇ278 per night
4.95 out of 5 average rating, 122 reviews
Guest favorite
Home in Hartford
The Quechee Haus: VT Retreat with Outdoor Hot Tub
Oct 17 – 24
ﺩ.ﺇ2,007 per night
4.96 out of 5 average rating, 125 reviews
Guest favorite
Barn in Chester
Inviting studio apartment above barn in Vermont
Aug 4 – 11
ﺩ.ﺇ324 per night
4.99 out of 5 average rating, 485 reviews
Guest favorite
Guest suite in Hartford
Sunny Side Airbnb (dog friendly)
Jun 16 – 23
ﺩ.ﺇ366 per night
4.92 out of 5 average rating, 308 reviews
Guest favorite
Guesthouse in Hartland
Yurt In The Woods - Private Refuge
Dec 24 – 31
ﺩ.ﺇ588 per night
4.95 out of 5 average rating, 909 reviews
Guest favorite
Cabin in Woodstock
Cozy Log Cabin, Peaceful Retreat
Jul 4 – 11
ﺩ.ﺇ969 per night
4.98 out of 5 average rating, 174 reviews
Guest favorite
Chalet in Royalton
Scandinavian design Chalet w/ private hiking trail
Jan 9 – 16
ﺩ.ﺇ1,550 per night
4.93 out of 5 average rating, 113 reviews
Guest favorite
Tiny home in Woodstock
The Cluck House
Oct 21 – 28
ﺩ.ﺇ551 per night
4.99 out of 5 average rating, 117 reviews
Guest favorite
Cabin in Royalton
Genuine Vermont Sugar House on 70 peaceful acres.
Aug 9 – 16
ﺩ.ﺇ496 per night
4.99 out of 5 average rating, 174 reviews
Guest favorite
Cabin in Randolph
Secluded Log Home on 109 Acre Natural Wonderland!
Mar 24 – 31
ﺩ.ﺇ418 per night
4.95 out of 5 average rating, 185 reviews
Guest favorite
Cottage in Reading
Shattuck Hill Cottage
Oct 24 – 31
ﺩ.ﺇ367 per night
4.95 out of 5 average rating, 128 reviews

Other great vacation rentals in Woodstock

Guest favorite
Home in West Windsor
Birdie's Nest Guesthouse
Jul 26 – Aug 2
ﺩ.ﺇ467 per night
4.96 out of 5 average rating, 49 reviews
Guest favorite
Home in Woodstock
Pet Friendly Woodstock Home; Minutes to Killington
Jun 1 – 8
ﺩ.ﺇ571 per night
4.98 out of 5 average rating, 41 reviews
Guest favorite
Home in Woodstock
Winterfound Farm - renovated VT barn & farm stay
Oct 26 – Nov 2
ﺩ.ﺇ1,879 per night
5.0 out of 5 average rating, 6 reviews
Guest favorite
Vacation home in Woodstock
Peaceful 3BR Chalet central to ski resorts
Apr 27 – May 4
ﺩ.ﺇ465 per night
5.0 out of 5 average rating, 62 reviews
Guest favorite
Cottage in Woodstock
Modern Cottage Near Skiing, Trails & Fine Dining
Apr 10 – 17
ﺩ.ﺇ922 per night
5.0 out of 5 average rating, 14 reviews
Guest favorite
Home in Bridgewater
Luxurious family retreat home in the mountains
Jun 2 – 9
ﺩ.ﺇ2,314 per night
4.9 out of 5 average rating, 40 reviews
Guest favorite
Cottage in Hartland
Hartland - Adorable Cottage w/FIOS - Pet Friendly
Apr 13 – 20
ﺩ.ﺇ555 per night
4.92 out of 5 average rating, 83 reviews
Guest favorite
Home in Woodstock
Woodstock VT Family Friendly, Four Season Getaway
Dec 26 – Jan 2
ﺩ.ﺇ1,665 per night
5.0 out of 5 average rating, 14 reviews
Guest favorite
Tiny home in Chester
Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo
Feb 12 – 19
ﺩ.ﺇ815 per night
5.0 out of 5 average rating, 73 reviews
Guest favorite
Home in Hartford
Luxury Barn w/ Hot Tub, Sauna, Mtn Views
Jan 30 – Feb 6
ﺩ.ﺇ1,739 per night
4.98 out of 5 average rating, 86 reviews
Guest favorite
Barn in Bridgewater
Incredible Riverfront Farmhouse mins to Woodstock
Jul 15 – 22
ﺩ.ﺇ1,405 per night
5.0 out of 5 average rating, 49 reviews
Guest favorite
Apartment in Hartland
Hearth House Farm
Jan 6 – 13
ﺩ.ﺇ478 per night
4.96 out of 5 average rating, 99 reviews

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

ﺩ.ﺇ331 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 280 vacation rentals in Woodstock, over 10 vacation rentals in South Woodstock, and over 220 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 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 bed and breakfast rentals in Woodstock have wifi?

    Absolutely! We offer over 20 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 apartment rentals in Woodstock?

    Woodstock has more than 10 family-friendly apartment rentals. 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