Known for its rich culture, heritage, and scenic vistas - Woodstock, Vermont has it all. Situated at the shire town (county seat) of Windsor County, Vermont has a vivid four-season goal that saddles the soul of its economy. Whether you have come here for the scenery or the historical culture of this place, one thing is for sure - relaxation and satisfaction will be at your hands. So what are you waiting for? Come walk the village, meander the byways of Vermont’s farmland, and experience the fortunes of Woodstock. There are many accommodations available here to suit every taste and budget. Scroll below and check out the best Vrbo vacation rentals in Woodstock, Vermont.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 23, 2024.
Why Trust Trip101?
✅ Over 50,000 articles reviewed and published by our experienced team
✅ Over 50 years of combined experience researching, writing and reviewing travel articles
✅ Over 40,000 hours spent on research and fact-checking from credible sources (last year’s data)
✅ Optimizing content from data-driven insights collected directly from users on our platform
✅ Focus on authentic and up-to-date information by collaborating with local guides, global travelers and other industry experts
✅ Long-standing partnerships with credible brands like Airbnb, Booking.com, Agoda, Expedia, GetYourGuide, Viator, RVShare and more
✅ Full disclosure on any partnerships or sponsored content
Trip101’s team of writers, editors, and content managers oversees the publication of all travel content, including destination guides, accommodation recommendations, and travel tips. They have extensive experience in the travel industry and no content, written or visual, gets published without a review. Many of our team’s work has also been featured in Travel+Leisure, National Today, The Indian Express, The Telegraph (India), Robb Report, The Adventure Handbook, Tripoto, Korea Tourism Organization, and Korean Ministry of Culture, Sports and Tourism. Some of them are also members of professional organizations like the Society of American Travel Writers and the International Travel Writers and Photographers Alliance.
Each member of the team follows Trip101's methodology and strict editorial guidelines to ensure accuracy, authenticity, and relevance.
1. Charming home surrounded by nature (from USD 562)
Built on a hill overlooking the picturesque town of S. Woodstock, this comfortable all-year home comes with a huge deck offering panoramic vistas of the Kedron Valley. The property is set in a rural area surrounded by fields, woods, and adjacent ranches. The house is built over two floors. The ground floor contains the living area, a kitchen, a dining area, one bedroom, and a full bath. The other three bedrooms can be found on the second floor. The house has all the modern amenities required for a comfortable stay.
Top guest reviews
Host:
Great communication with the owner Property is alwaysShe was always prompt to respond to any questions we hadThe property manager left us cheese and crackers upon our arrival and she was very responsive when questions aroseshe cares deeply about her guests experience and has made this lovely home into the quintessential Vermont charmerWe also had good contact with MaryLocation:
Lots of restaurants close by either in South Woodstock or in Woodstock itselfIt is quiet and private but only a mile from a lovely restaurant and the idyllic South Woodstock General Store (excellent grilled cheese sandwiches)It is only about 8-10 minutes to downtown Woodstock or the Farmer's MarketWe loved being surrounded by the library of books and spent a rainy winter day in front of the fire reading and playing gamesThis is really a wonderful house with an excellent location away from the crowds in WoodstockCleanliness:
It was clean and well appointedEverything was as clean and as tidy as could beLarge house that is comfortable impeccably clean and well keptThe perennial gardens are incredible and as thoughtfully composed as the inside of the houseThe house itself is furnished very well and is so clean and comfortableRead more reviewsAmenities & Room:
The kitchen is well appointedyour home provided a wonderful respite from downtown living in the southIt was immaculate from top to bottomIt was comfortable and spacious yet cozy and invitingMary had thought of everything
2. Two-story historic residence (from USD 277)
To make the most of your Woodstock holiday, relax and stay in this vacation rental situated in the historic Tribou Park. The home can accommodate four persons. It is equipped with a bedroom located on the second floor, a full-size bathroom and a half-bath. There are two porches with a grill for a barbeque, a full kitchen complete with the essentials needed for cooking, and lastly, there is a living room with comfortable sofas for relaxation. Restaurants, museums, and other attractions can be found in the vicinity.
Top guest reviews
Host:
The owner is very friendly and helpfulBrenda was super responsive to emails and very accommodatingWe loved everything about our experienceso when we arrived it could not have been cozier or more invitingWe couldn't find anything that she hadn't thought ofLocation:
Woodstock is quaint and the village green has activities all summerall of Woodstock's shops and eateries are within easy walking distanceThe property is right at the intersection of the main street going into town Very convenient and walkable to shops restaurants and tree lined streets for a run or walk Being the main way in and...Unfortunately it is at the junction of the main street in Woodstock and another busy routeThe location is prime; walking distance to anything in the villageCleanliness:
Beautifully decorated and maintained apartmentLarge 1/2 bath downstairs and another large full bath with both tub and shower upstairsI slept like a babyIt was beautifully decorated and the location was excellentThe location can't be beat From the unitRead more reviewsAmenities & Room:
Big kitchen fully stocked with everything you might need to cook Washer/dryer upstairs tooReally comfy bed upstairs with a huge walk-in closet (Was easy to take our dog on walks-The only small issue we had was the noise from big trucks on the highway outside our bedroom windows at nightThe apartment is very nicely appointed and lacks for NOTHING
3. Classic riverfront cottage (from USD 310)
If you wish to be one with nature, here is a cottage you should choose. Situated next to the Marsh-Billings-Rockefeller National Park the rental has easy access to miles of parkland with hiking, biking, and cross-country ski trails. This house can accommodate up to four persons, with a bedroom and an en suite bathroom and an open-plan living room overlooking the Ottaquechee River. This residential accommodation is ideal for soul searching.
Top guest reviews
Host:
A small mix up on the entry access code but owner was responsive and got us into the rental without delayWe did cook most of the time and the stove was greateven a ping pong table in the garageGreat location Owner was very responsive House was very clean Perfect for a coupleI'm already trying to figure out the next time I can get back (and thanks to management company who kept the driveway and walkway clear of iceLocation:
It was walking distance to downtown and National ParkThe house has a BBQ grill bikesOtherwise it was great location and apartmentWalking distance to walks hikesThe house is located in the amazingly quaint town of WoodstockRead more reviewsAmenities & Room:
The cottage is very comfortable and had everything that we needed An extra comfortable chair would be nicebringing in wonderful natural lightThe kitchen has everything one might need and plenty of room to move around in The living area has a cushy big couch where you can stretch out or prop your feet up (I agree with a previous review...but it was hot during our tripPerfect space exactly as described and in the photos
4. Quintessential log cabin (from USD 190)
Woodstock offers a large number of log cabins. Enjoy a special holiday amidst nature in this one-bedroom unit that can accommodate four guests. This rustic rental has top-class modern amenities like a TV, sofa beds, high-speed internet, and kitchen essentials. It is also a short walk away from business centers and restaurants. The amiable hosts are happy to help with any queries that you may have.
Top guest reviews
Host:
were super helpful in answering any questions we had and giving us advice about where to goWe were so grateful for the great advice from our host BobBob was so helpful and friendlyWe especially liked the restaurant he sent us toOwners met us when we arrived and gave us the run down on the apartmentLocation:
It is within walking distance to lots of cute resterauntsThere are fabulous restaurants in town and even a spa within walking distanceEvery detail is lovingly attended to and Bob and Sherry are a wealth of information about Woodstock and the surrounding area(Monday Night Trivia on Wednesday plus other events)Skiing at Suicde Six(closes at 3:30 in the winter)Live Music at Bentley'sCleanliness:
It was perfectly clean and tidyThe beautiful apartment was super cleanThe apartment was quiet stayed cool in very warm weather very clean and charmingIt was quiet and had beautiful viewsThe owners are wonderful and were extremely helpful without ever being intrusiveRead more reviewsAmenities & Room:
The photos of this apartment do not do it- I agree with the author in the review above - the pictures do not do it justice at allThe apt has everything you need to feel at homeWe just stayed at the apartment and found it to be equipped with everything you needI couldn't have dreamed up a more perfect gift
5. Modern residence with a private entrance
To maximize the experience of being one with nature, this vacation rental is equipped with a bedroom, a bathroom, and a kitchen. The kitchen is ideal for cooking and equipped with all the necessary appliances. If you are craving for a calm and tranquil stay, this is the perfect place. With its serene and peaceful location, you will soon feel rejuvenated and relaxed. Guests can indulge in many activities while staying here such as hiking, biking or simply brisk walking. The pure oxygen and fresh air is an added bonus.
Top guest reviews
Host:
Every suggestion they gave us worked out incredibly wellThey are knowledgeable gracious and gave us great advice about things to do and places to eat in Woodstock Hanover Middlebury and even into MaineThey responded quickly to our inquiries and made our check-in very simple even letting us check in earlythey are very helpful and responsiveThe owner was quick to respond to our questions and made sure we knew all of the features of the unitLocation:
The location of the unit is within walking distance of the village greenReally pretty quiet spot and a nice location to walk into townbut it's well litStepping across the property's stone wall takes you to trails on Mt PegThe house is a short drive to KillingtonCleanliness:
We loved having a washer and dryer to refresh our clothes after a long road tripThe unit was very clean and stocked with the standard kitchen items needed but also provided a washer and dryerRead more reviewsAmenities & Room:
The kitchen is well stocked with supplies to cook mealsalthough we did not because it was too cold outside SamThe apartment itself was very comfortable: the fixtures and furniture are all clean new and modernA two-minute drive down the hill takes you into town; a walk down is fineIt has all the amenities - wifi
6. Country home with three decks (from USD 238)
This historic country home is a sight to behold. Recently renovated to include modern features, it can accommodate eight guests in its three bedrooms. The bathrooms are well stocked and feature walk-in showers. The well-equipped kitchen is ideal for cooking and fitted with all the necessary appliances. The adjoining dining room can seat six people. Commune with nature and relax on the three outdoor decks. The home is conveniently located near the downtown area. Guests can easily visit the various attractions, restaurants, and cafes in the vibrant town center.
Top guest reviews
Host:
Some of the bedrooms had no curtains and the morning sun woke us up at a very early hourThe house is very family friendly and the fire kept us warm as it snowed outsideSarah and Ryan quickly and ably responded to issues that almost inevitably accompany checking into an unfamiliar propertythe the rest of us were too overwhelmed with the home's charm to notice anything amissAll in all a very nice house with issues that were addressedLocation:
It's within a short walk to the Green with all cute shops galleries and restaurantsIt's a really short walk right into townThe living spaces are very nice in this house with lots of good chairs / sofas and a lovely surroundingthe house - location is great (right off the green walking distance to everything in town)We enjoyed our stay at this beautiful 3 bedroom house on a quiet street in Woodstock Location can't be beatCleanliness:
I can't say enough aboutAll the bathrooms were apparently not clean when we arrived and the kitchen was quite grimyAll the bathrooms are updated and very niceRead more reviewsAmenities & Room:
The master bedroom is comfortable but the bed in the second queen size room is extremely creaky when a person moves aroundThe hot water heater could not keep up with the demand of six people taking showers; once we ran out of water (after three showers)The kitchen is well outfittedIt was spacious comfy and very well equippedAlthough we used car as weather was raining on and off couldnt have been better Ferns and gardens
7. Elegant and serene cottage
Enjoy your stay at Woodstock, Vermont at this cottage, located 2 miles (3.2 km) from the Woodstock Village Green. The accommodation includes one bedroom with an attached bathroom. The living room is furnished with televisions, a sofa for comfort and other amenities include a high-speed internet connection, air conditioning, heater, and a fireplace. Admire the picturesque views of hills, trees, a pond from your cottage. Restaurants and other entertainment options are just a short drive away and easily accessible from the property.
Top guest reviews
Host:
Elizabeth had the refrigerator well stocked and made us cookiesElizabeth and Jason were great hostsWe also enjoyed having the chickens visit usSuch gracious hosts adorable free range chickens visiting our doorstep to say hello daily beautiful grounds cozy comfortable cottageBe sure and try out Worthy Kitchen & Mon Vert CafeLocation:
The cottage is between Woodstock and QueecheWe loved the peace and quiet after a noisy winter in NYCConveniently located to Woodstock Quechee and HanoverOtherwise the location is ideal super close to Quechee and Woodstock centerWonderful cottage in a beautiful settingCleanliness:
Cottage and grounds are immaculately clean and well-maintainedThis is a beautiful cottage set in scenic grounds The cottage is sparkling clean and comfortable with everything you require for your stayRead more reviewsAmenities & Room:
It was very peaceful at night and the bed was very comfyThe house is well equipped and air-conditioned for the few times we neededThe cottage was as advertised comfortable and well situated to reach the Town of Woodstock and surrounding areaIt's right down the street and excellentThe cottage is located close to Rte 4 and traffic noise is audible from the bedroom
8. Cozy bungalow with a sauna in the woods (from USD 369)
Time to relax, unwind and de-stress from your hectic routine. This is the place to go if you’re looking to get away from it all. The bungalow is equipped with two bedrooms and two bathrooms. The sauna at the property is a special addition. The rental can accommodate six guests and ensures satisfaction and comfort. Surrounded by acres of greenery, hiking and biking activities are a part and parcel of a stay in Woodstock.
Top guest reviews
Host:
She was incredibly helpful and gave us wonderful suggestions about the Woodstock communitylovely thoughtful and attentive hostDelightful spot refined property fantastically welcoming ownerThis property was even more beautiful in personYou will fall in love with this house and be very happy with KatLocation:
This place is just minutes from Woodstock located on a beautiful tree lined bike routeThe location and the house itself are just fabulousthe location was right outside of Woodstock and a short drive to Mt KillingtonGreat house and great locationWhat a lovely way to pass a few days in summer in VermontCleanliness:
The house was comfortable and cleanThe house was very inviting with many personal touchesThis place is super clean and fully stockedall of the linens and furniture smelled fresh and were also incredibly cleanRead more reviewsAmenities & Room:
The mattress on the king in the master bedroom is the most comfortable I've slept on in a long timeThe living area furniture is comfortable and there is nothing like sitting in front of the gas fireplace on a cool eveningHaving access to bikes and plenty of outdoor space was a real bonusThe kitchen is extraordinarily well equipped with quality pots pans and utensils and basic suppliesVery clean and well stocked with everything you need to cook up a storm
9. Quiet residential home (from USD 273)
If you are craving a calm and tranquil stay, this is the perfect place be. This apartment is within walking distance to the many places of interest like restaurants and cafes. With the view from your backyard overlooking the woods, this rental is a place to relax and enjoy what nature has to offer. Complete with a bedroom and a bathroom the apartment can accommodate up to four persons. There is a fully equipped kitchen where one can whip up gourmet meals.
Top guest reviews
Host:
microwave and all the utensils to go along with)cozy and had anything we needed and morehome away from home Clay and Brenda were very helpful when we needed somethingWhile we were attached to a house we never felt like anyone was close by - very private TVs in the main room as well asMt Tom Clay and Brenda were very friendly and accommodatingLocation:
Woodstock has a great downtown with lots of restaurantsWoodstock and surroundings are idyllicGreat place-and our dog liked it too Perfect Woodstock locationIt was a quick walk into town and under 30 minutes to Killington White River Junction and many other great thingsBeautiful setting and Clay and Brenda are exceptional hostsRead more reviewsAmenities & Room:
The kitchen had all the ammenities spacious rooms and a great bathroomThe wall of windows was fantastic to look out at in the morning and at night we could snuggle up in the living room or bedroom and watch tvEverything from appliances to the furniture are updated and comfortableQuiet and cozy with the forest on one side and easy access to Woodstock amenities on the otherThe Apartment at Prospect Place exceeded our expectations All of the amenities of home in an efficiency apartment The private deck added an extra space to enjoy the beauty of Summer in VT
10. Family-friendly country home (from USD 398)
Stay in this delightful country home that has all the essentials for a home-away-from-home experience. This residence is good for families on vacation to Woodstock, Vermont, and can accommodate up to six persons. It has a total of three bedrooms and two bathrooms, complete with a hot tub. The chef’s kitchen is well equipped with new stainless steel appliances. The property is located about 1.7 miles (2.7 km) from the Woodstock Village and a 20 minutes’ drive away from a ski resort.
Top guest reviews
Host:
The owner was helpful and friendlyshe is darling and attentiveMatt made sure we had his cell number JUST in case we got stuck somewhere in town such amazing hostsa hot tub and friendly horsesespecially the owners horses who greeted us in the morningLocation:
Beautiful setting in idyllic village of WoodstockThe location is great with Woodstock center a very short drive away and lots to do in the surrounding areaThe hike up to Mt Tom in town was beautiful Dinner at the Prince and Pauper Simon Pearce and Bentley'sWe LOVED the fact that it was a 1 minute drive to the newly opened Farmers Market and a 3 minute drive to the greenWe enjoyed the wood stove and outside little chimenea walked to town for breakfast at the Mon Vert CafeCleanliness:
Everything was very thoughtfully stockedThe home was well appointed and exactly as it was described VRBOWe had everything we needed and hope to use the property again in the futureRead more reviewsAmenities & Room:
nice kitchen table to read the paper atimmaculate comfortable with everything you needThe kitchen is extremely well equipped making cooking easyHouse is comfortable and well appointedWe enjoyed playing in the spacious yard (especially during the random thunder storms)
Experience the most relaxing vacation in Woodstock, Vermont
The above-listed vacation rentals in Woodstock, Vermont will surely take care of your accommodation needs. All you are required to do now is book yourself a holiday to Woodstock with family and friends.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
