Boutique hotels in Woodstock

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Popular amenities for Woodstock boutique hotels

Vacation rentals in Woodstock

Top guest favorite
Home in Pomfret
5 out of 5 average rating, 107 reviews

Private Vermont Oasis Under 10 Mins from Woodstock

CathieRating, 5 stars3 weeks ago
Adam and Nicole's house is wonderful! Great view, spacious, and so clean. We all felt very comfortable and cozy. Great amenities, and a nice deck that unfortunately we didn't get to enjoy because of the rainy weather! Still, we enjoyed our stay and didn't let the rain dampen our spirits. Hosts were both very responsive, no issues with check in. Highly recommend if you're looking for something off the beaten path and quiet, but close enough to restaurants and sight-seeing. Thumbs up for sure!
Guest favorite
Home in Barnard
4.99 out of 5 average rating, 146 reviews

The Looking Glass, a modernistic escape

SandyRating, 5 stars2 weeks ago
Overall we very much enjoyed modern rural space. Kiss the Cow farm about 5min drive was amazing& we got most all main food there w/ additional items from Barnard General Store. Spices/ cookware were very good - we brought nonstick pans& 1 knife to supplement. Plenty bowls, measuring cups/spoons, maybe a set of tom collins glasses would be nice albeit stemless wine and rocks glasses available. Needs garlic/onion powder. Tub was amazing/ upstairs bathroom a true getaway/ relaxing space. It was as pictured albeit note spiral staircase &open grated flooring upstairs. Plenty of windows albeit not much cross breeze so think ahead if bring own fan and/or start A/C before get too warm. I would say you must have an SUV year round for this rental - surrounding roads/ driveway are a good distance on rough dirt/gravel - traversable yet a sportier car with low profile tires/ ground clearance would not work. We enjoyed simply walking driveway& East Barnard Rd. Barnard Inn restaurant worth it.
Top guest favorite
Barn in Woodstock
4.99 out of 5 average rating, 154 reviews

Stunning Converted Barn Home 3-bed 2 bath

CarolRating, 5 stars5 days ago
It was perfect. The location was amazing and the accommodations were very comfortable. I would highly recommend the barn. We were there to celebrate my son's graduation from Tuck and it made the occasion perfect. Our small family gathered and cooked on the deck and enjoyed the view. I would certainly rent this location again.
Guest favorite
Cottage in Hartland
4.93 out of 5 average rating, 119 reviews

Adorable Dog Friendly Cottage w/FIOS

DylanRating, 5 stars4 days ago
Very cute cottage with lots of privacy and beautiful surroundings. Lulu was friendly and very accommodating with everything.
Top guest favorite
Home in Woodstock
5 out of 5 average rating, 133 reviews

Beautiful Woodstock Home-Perfect for entertaining

EmmaRating, 5 stars5 months ago
We had a fantastic stay at this beautiful home. We came with our 6 month old and 3 year old daughters and pup. There was plenty of space for the whole family and very kid friendly. We were saying when we were there that it would have been amazing with a group of friends for a girls weekend too! Beautiful spot where you feel like you’re deep in the Vermont woods but super close to downtown Woodstock. Would love to stay again if available!
Top guest favorite
Cabin in West Windsor
4.97 out of 5 average rating, 249 reviews

Sunset Cabin - your private romantic hideaway

CassandraRating, 5 stars1 week ago
We had a fantastic stay at this private cabin in Vermont! The place was exactly what we were hoping for - peaceful, cozy, and surrounded by nature. The cabin was spotless and clearly well taken care of, with everything we needed for a comfortable stay. The host was super responsive and friendly! It’s the perfect spot if you’re looking to unplug and relax. I would definitely recommend this place to anyone looking for a private getaway in Vermont. Hope to return soon!
Guest favorite
Cabin in Rochester
4.95 out of 5 average rating, 473 reviews

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

KayelynnRating, 5 stars4 days ago
Agnes’s place was so cute and perfect for our vacation! She communicated everything we needed to know and made sure our stay was perfect. Would recommend this place to any couple looking to explore Vermont :)
Top guest favorite
Home in West Windsor
4.98 out of 5 average rating, 124 reviews

Birdie's Nest Guesthouse

KyraRating, 5 stars3 weeks ago
Loved our stay! Everything was cozy and easy; no issues at all. The heated bathroom floor ended up being one of our favorite parts (so nice!), and the whole place just felt super relaxing. Didn’t need to contact the host because everything was smooth from start to finish. Would definitely come back!

Other great vacation rentals in Woodstock

Top guest favorite
Tiny home in Hartland
4.96 out of 5 average rating, 193 reviews

Cabin on the Hill

NicoleRating, 5 stars1 week ago
Love, love, love Julie’s place. It is the perfect weekend getaway. Incredibly peaceful and beautiful surroundings. We will be back again!
Guest favorite
Apartment in Hartland
4.88 out of 5 average rating, 470 reviews

Sunny Studio Apartment in Hartland

AlexandraRating, 5 stars3 months ago
It is a nice place to stay, conveniently located near ski resorts with easy access to the highway. It was perfect for our family of three as a seasonal rental for skiing at Saskadena Six. Nancy was friendly and highly responsive to our requests, making our stay even more enjoyable. Overall, we were very happy with our experience and would highly recommend it!
Top guest favorite
Cottage in Hartland
4.97 out of 5 average rating, 457 reviews

Breeze Hill Cottage

EmilyRating, 5 stars3 weeks ago
Breeze Hill Cottage was very cozy and comfortable. A fun farmhouse feel in the beautiful countryside! Heidi was very responsive (and prompt!) and super nice. We thoroughly enjoyed our stay and look forward to booking again in the future!
Top guest favorite
Cottage in Windsor
4.97 out of 5 average rating, 393 reviews

Ogden's Mill Farm

AndrewRating, 5 stars6 days ago
The Cabin at Ogden's Mill Farm is spacious comfortable and in a beautiful location. An ideal place for relaxing either inside or outside on the porch overlooking the garden. Rhubarb the dog came to visit a few times and is always friendly and happy to walk around the Cider Mill and lake with you. Jamie is friendly and helpful and we enjoyed having a chat and recieving useful advice from her.
Guest favorite
Cabin in Woodstock
4.95 out of 5 average rating, 199 reviews

Hideaway Cabin by the Stream on 27 Acres

JenniferRating, 5 stars1 week ago
Our stay was incredible! The view by the stream was amazing, everything was so peaceful and perfect. Inside the cabin was exactly what we expected, very homey, everything we needed. We loved the walls lined with books! Kevin was very attentive towards what we needed - it stormed all day Saturday and he brought a second heater for us because the temperature dropped, which with that and the gas fireplace, kept the place perfectly warm and comfortable. He was also very accommodating in allowing us to stay an extra night since our plans of hiking all weekend were thwarted by the rain. We went for my husband's 40th birthday and i couldn't have picked a better place to get away from the stress of life. We plan on going back for sure!
Guest favorite
Guesthouse in Woodstock
4.98 out of 5 average rating, 242 reviews

Cozy Little Spot (Self Check-in)

StevenRating, 5 stars3 weeks ago
The property was easy to find. Cabin was rustic and very comfortable. It was secluded in a wooded area overlooking a rushing brook. Fresh bedding and new window shades made for great sleeping! Excellent communication with our host and clearly his top priority was that we were comfortable in the accommodations. We would definitely stay here again.
Top guest favorite
Apartment in Woodstock
4.95 out of 5 average rating, 197 reviews

LOG HOME APARTMENT IN WOODST. VILLAGE 3 night min.

AllieRating, 5 stars2 months ago
We absolutely loved our stay with Bob and Sherry. They were so kind and attentive on the app, providing recommendations and checking in frequently when the weather turned on us. Although we were technically in their home, it still felt very private. The apartment is beautifully done and I’m obsessed with the pine wood everywhere. We would absolutely return and cannot recommend this little place highly enough!
Guest favorite
Tiny home in Woodstock
4.99 out of 5 average rating, 136 reviews

The Cluck House

JohnRating, 5 stars1 week ago
I really loved staying at the Cluckhouse. It was truly so beautiful and peaceful, a tranquil space that honestly was almost fairytale beautiful (even in the quiet rain of one of the days), while also being only 10 mins from the town Woodstock. Tina was an amazing host; she reached out well before I arrived with directions and suggestions, she was extremely thoughtful once I arrived, and, most importantly, a wonderful person with a calm peaceful energy; I really enjoyed talking to Tina whenever I’d come thru the kitchen. I’d love to stay here again

Quick stats about vacation rentals in Woodstock

  • Total rentals

    180 properties

  • Nightly prices starting at

    G$18,823 GYD before taxes and fees

  • Total number of reviews

    6.6K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

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 320 vacation rentals in Village of Woodstock, over 10 vacation rentals in South Woodstock, and over 260 vacation rentals in Taftsville.

  • Are there vacation rentals with a dedicated workspace in Woodstock?

    Yes! Work meets play with ease at over 80 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 70 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in bed and breakfast rentals in Woodstock?

    Experience the best of Woodstock with our bed and breakfast 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 20 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 70 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 10 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