Cozy and Charming Airbnbs in and Around Woodstock, VT

By Kelley Boymer
18 Aug 2022

Woodstock, Vermont is a beautiful, quintessential, charming town that has become a popular destination for many due to its picturesque, quaint village, unique shops, delightful restaurants and charming lodging. While there are many inns, hotels and b&b’s to stay in while in Woodstock, many seek a stay at an Airbnb due to their privacy, unique amenities, kitchens, living spaces and overall affordability. In addition, airbnb’s provide a more intimate experience to “live like a local”.

If you are traveling to Woodstock and looking for a cozy and charming spot to base your stay look no further! Today we are sharing the best airbnbs in and around Woodstock.

Cozy and Charming Airbnbs in and Around Woodstock, VT

Stunning Converted Barn Home (3-bed, 2 bath)

If you are looking to splurge and be pampered, this charming barn home is the perfect spot for you. With everything from a chef’s kitchen to a stone fireplace, high end furnishings, a deck with picturesque views, outdoor fire pit and gorgeous fields for walking and exploring. This barn home is off the beaten path in the beautiful town of South Woodstock, just a 10 minute drive from the Woodstock Village. Amenities include washer and dryer, wifi, mountain views, indoor wood burning fireplace and TV. This property accommodates 6 guests with 3 bedrooms, 4 beds and 2 baths. The barn home is not pet friendly.

THE LOFT, Stunning Views from a timber Framed Barn

The Loft is another stunning home to hunker down while in Woodstock. This cathedral loft is bright and airy while also being cozy. This space accommodates 5 guests with 2 bedrooms, 2 beds and 1 bath. Amenities include mountain views, wifi, washer and dryer, A.C., private patio/balcony, fireplace, TV and a kitchen. Located just 3.5 miles from the Woodstock village, the loft provides all the convenience and coziness you need for a Vermont getaway!

Elegant Village Apartment

This Elegant Village Apartment is both affordable and conveniently located right in the village of Woodstock. It sleeps 4 guests with 2 bedrooms, 3 beds and 1 bath. This newly renovated space has a washer and dryer, wifi and piano amongst other amenities including a refrigerator, hair dryer, highchair and microwave. The perfect place to base your stay to allow for walkability in the village to enjoy all the shopping and dining your heart desires!

The Cluck House

For a small, simple, sweet and affordable stay, try The Cluck House just 3 miles outside of the village of Woodstock. This home accommodates 2 guests with 1 bedroom and bathroom. Amenities include: pac ‘n play, backyard, refrigerator, kitchenette and coffee-maker. This is a great escape into the countryside, but only available seasonally. Pet friendly!

[KAB-IN] A Whimsical Log Cabin in Woodstock, VT

This whimsical Log Cabin is the perfect place to stay to get the full Vermont experience. Located 2.5 miles from the village, the [Kab-in] provides the privacy and intimacy of a remote vacation with the convenience of proximity. Expect incredible views, rustic beauty and modern amenities. This 1 bedroom, 1 bed and 1 bathroom home accommodates 4 people with an additional loft space and blow up mattresses for extra children/guests. Amenities include washer and dryer, patio/balcony, indoor fireplace, pac ‘n play.

Lovely One Bedroom Apartment

For peace and quiet, stay at this beautiful apartment nestled amongst the woods just 3.5 miles outside the Woodstock village. Amenities include garden views, kitchen, refrigerator, wifi and TV. The apartment accommodates 2 guests with 1 bedroom and 1 bath. An affordable stay just outside the village for a couple or single traveler.

Cheerful, Restored 1940s Cape- 5 mins to Woodstock

For larger groups, this newly restored 1940s Cape is a lovely place to stay while in Woodstock. It accommodates 8 guests with 3 bedrooms, 5 beds and 2 baths. Located in South Pomfret just a 5 minute drive from the village of Woodstock, this is the perfect place unwind and relax. Located within walking distance of Teago Store, Saskadena Six and Artistree Arts Center. Amenities include mountain views, kitchen, work spaces, wifi, TV, outdoor fire pit, indoor fireplace, 3-season porch, washer and dryer.

Log Home Apartment in Woodstock Village

Another beautiful Log Home to base your stay in Woodstock. This home accommodates 4 people with 1 bedroom, 2 beds and 1 bathroom. Includes a full kitchen and laundry with gorgeous garden and mountain views. Also includes wifi, free parking, A.C., kitchen, TV and children’s books and toys. Located just a few minutes from the village of Woodstock this a great location to cozy up for your stay.

Cottage Near Woodstock

Located just outside of Woodstock in Pomfret, Vermont, this beautiful newly renovated Cottage accommodates 2 guests with 1 bed, 1 bath and a studio. Amenities include a kitchen, TV, patio with outdoor fire pit, deck, AC, refridgerator, free parking and wifi. A lovely place to stay within a short distance from the village.

River St. Apartment

Located right in downtown Woodstock, this River st. apartment is the perfect place to lay your head for the convenience of a downtown adventure. This apartment accommodates, 2 guests with 1 bedroom and 1 bath. Amenities include a kitchen, backyard, parking, wifi, TV, indoor fireplace and refrigerator. River street is a beautiful picturesque street off of the main village for beautiful walks and admiring gorgeous homes.

Have you stayed at an airbnb in or around Woodstock? We would love for you to share your recommendations in the comments below!

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