Bed and breakfast holiday rentals in Woodstock

Private room in West Windsor

The charming two-story Vermont cape house is enveloped in lush greenery and blooming wildflowers, creating a picturesque setting. The exterior features a brown roof with dormer windows and a welcoming porch, nestled under a bright blue sky with scattered clouds.

Thorny Hills Farm

Private upstairs suite that sleeps up to 6 people. 1 bedroom with a queen sized bed & a bedroom suite with 4 single beds. Sitting area with tables allow for relaxing or group meals. Private bath serves the suite. Mini frig, microwave & coffee maker with grill outside. Private entrance & patio. Perfect for local horse events. No smokers. NOT suitable for young children under 10. No infants. Check in is 4PM but can be adjusted if needed. Check out is 10AM. Additional guests $35/night

FamilyLocationAir conditioning

4.85 out of 5 average rating, 110 reviews

Private room in South Acworth

An aerial view showcases the earth-sheltered home surrounded by rolling hills and trees. The open landscape features a winding road and neighboring structures in the distance. The well-maintained grounds include landscaped areas leading to the house, highlighting a tranquil and natural setting.

13 Hills - A Unique Earth-Sheltered Destination

Welcome to 13 Hills! Set in the picturesque Monadnock region, our earth-sheltered, open concept home offers magnificent views, serenity, and comfort. With an 1100 square foot terrace with firepit and year-round hot tub, and pool room with darts, this is not your usual B&B. Your room has a king-size memory foam bed, bureau, 42 inch TV, DVD & internet services, a full bath with tiled shower, a fridge with freezer, microwave and panoramic vistas. Full breakfasts of your choosing are our specialty!

FamilyLocationBreakfast

4.98 out of 5 average rating, 167 reviews

4.98 out of 5 average rating, 542 reviews

A cozy fireplace is centered in a spacious area, framed by elegant white walls and a wooden floor. A comfortable chair with green upholstery is positioned nearby, offering a welcoming spot to relax. A doorway leads to another room, enhancing the suite's layout.

Private room in Hartland

Spooner House - Atwater Room with Clawfoot Tub

The Spooner House – your retreat in the Upper Valley. This spacious suite features a cozy fireplace, mountain views, and a private bathroom with a clawfoot tub and shower. Enjoy the luxurious king-sized bed and serene ambiance. Located just 15 minutes from Quechee, Norwich, Hanover, and Lebanon, and close to Woodstock (25 min) and Killington (39 min). Your stay includes a self-serve breakfast with granola, yogurt, fruit, espresso drinks, and tea. You'll also have access to the guest kitchen.

LocationFamilyEV charging

A two-story cabin is surrounded by a blanket of fresh snow, with trees in the background and a clear blue sky above. The building features large windows, showcasing a sloped roof and a stone chimney. The pathway is partially cleared, leading to the entrance.

Cabin in Peru

Renovated new rental. Clean & comfy family home.

Our family friendly home is located in a desirable location, situated on a private road and beautiful setting. Peru, VT is minutes to Manchester, Bromley, Stratton, Okemo, and Magic Mnts. Renovated in 2016, our home has a gourmet kitchen, new bathrooms, washer/dryer, double sided fireplace, woodburning stove, wireless, and great room with HDTV dish network. All beds are new, and/or protected with "sleep tite" pillow & mattress protectors. Pillows are comfortable, blankets are soft and new.

LocationFamilyLayout

5.0 out of 5 average rating, 8 reviews

Private room in Bridgewater

A spacious house sits nestled among trees, showcasing large windows that provide ample natural light. A deck with an umbrella overlooks a well-maintained lawn. The scene is set against a backdrop of colorful foliage and a sky painted with soft clouds.

MT Retreat / Killington, Woodstock, Rutland, Okemo

We also offer our beautiful grounds as a venue for tented events. Bewitching views. Quiet, private suite. C. bkfst. Winter garage! COVID: “VT Forward” guidelines followed. Consider a private cooking class from award-winning Chef Ted and enjoy the foods of your labor in a lovely natural setting. BYOB. See Odyssey Events VT & Airbnb Experiences for cooking options. FYI, Bedroom size: 9' x 14'. Adjoining bathroom: 8' x 9'. The ante-room/office: 8' x 12', which is also yours to use.

LocationFamilySkiing

4.99 out of 5 average rating, 182 reviews

4.95 out of 5 average rating, 60 reviews

A handsome Federal-style home built in 1827 is showcased amid colorful autumn foliage. The brick exterior is complemented by large windows and classic features, while trees with vibrant leaves frame the entrance, enhancing the seasonal charm.

Guest suite in Weybridge

Middlebury Private Suite, walk to campus.

A pleasant walk to Middlebury town and college from this handsome 1827 Federal home which is licensed with the state. The suite has two bedrooms with one private bathroom and it’s own entrance. Each room has a queen bed with a comfortable mattress fitted with sun dried cotton sheets. The suite has a small refrigerator, microwave, electric kettle and French press. If the reservation is for 2 persons but both bedrooms are required, there is an additional $80 per night charge.

ValueLocationCheckout

4.98 out of 5 average rating, 248 reviews

Home in Antrim

HotTub FirePit Games Huge Backyard Family Friendly

The ultimate experience for couples & families 5-10min from hiking trails & ski resorts A Mile from Gregg Lake Beach ALL YEAR PRIVATE/SECLUDED HOT TUB Grill, Hammock, Gym equipment XBox Series S, Life Size Janga, Yahtzee, Darts, Corn Hole, ping pong table, mini pool table Luxury KING PURPLE Brand Mattresses in every bedroom for the best nights rest with individual mini splits for optimal comfort Fully stocked kitchen High speed WiFi, house on 2 private acres

ValueFamilySkiing

4.96 out of 5 average rating, 441 reviews

A serene home is framed by vibrant autumn foliage, showcasing a variety of orange and yellow trees. A white fence lines the property, while a lawn extends in the foreground, under a clear blue sky.

Private room in Wells

Endless Brook Farm B&B w Sauna, Hot Tub, Breakfast

Our home is located in a quiet, beautiful valley, surrounded by 175 acres of gardens, fields, hills, trails, streams, ponds and woods. Our bedrooms are bright and airy, with private bathroom upstairs on your own floor. Breakfast is provided each day -- all natural foods, special diets accommodated. 3-5 mins from Slate Valley Trails and Lake St. Catherine/State Park. 5 mins to Wells center. 10 mins to Poultney. 30 mins to Manchester or Rutland, VT.

FamilyValueHot tub

Private room in Rockingham

A vintage bedroom features a large double bed adorned with a floral patterned coverlet. Elegant antique furniture includes a dresser and two ornate lamps. Softly colored walls complement a decorative ceiling fixture. Two area rugs add warmth, and a small wooden bench is positioned against the wall.

Eva Blake House-Margaret's Room

Do you like the experience of staying in historic homes? Welcome to the Eva Blake House. A full menu breakfast is served in our dining room between 8 and 10 AM. Three common areas. Abundant amenities. A walk or short drive to The Square with its shops, art galleries, restaurants and our 1927 Opera House movie theater. Margaret's Room has one double bed. A walk down the hall: your large, private bathroom with walk in shower.

FamilyValueAccess

5.0 out of 5 average rating, 139 reviews

Private room in Middletown Springs

The Slate Rooms at Brigid's Crossing

Welcome to our Victorian home, where 19th-century charm meets modern comfort. This private suite includes two bedrooms—one with a queen bed and one with a full—and a full bathroom exclusively for your group. Located in a classic Vermont village, it's a cozy home base for skiing, mountain biking, fall foliage, and exploring the area. After a day of adventure, relax in the quiet elegance of our classic Vermont guesthouse.

ValueLocationBreakfast

4.76 out of 5 average rating, 100 reviews

5.0 out of 5 average rating, 9 reviews

The image captures a serene view of Lake Sunapee, showcasing calm waters reflecting the clear blue sky. Lush green hills line the shoreline, creating a harmonious natural setting that invites relaxation and appreciation of the outdoors.

Cottage in Newbury

Longview Cottage on Lake Sunapee

Enjoy wonderful summertime moments and make everlasting memories with loved ones, family and friends at this charming historic cottage built in the 1890’s. Relax at one of the most beautiful locations on Lake Sunapee, with long open 180 degree views of the pristine lake, rolling tree covered hillsides, Mount Sunapee, and the Fells Estate, an 83 acre nature preserve with undeveloped shoreline.

LocationFamilyView

4.98 out of 5 average rating, 146 reviews

Private room in Enfield

Charles Hewes Room- Shaker Hill B&B

Charles Hewes Room- Named for the first occupant of the house, the room has a queen-sized bed with an antique headboard, wide board floors, comfortable chair and a large private bathroom. Decorated in forest greens with cream accents, this room receives morning sun. The room includes breakfast. *A rollaway is available for this room. Please inquire. There is a small additional fee.

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Popular amenities for Woodstock bed and breakfasts

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly Bed and Breakfasts

4.96 out of 5 average rating, 154 reviews

A Victorian-style house with a broad front porch is depicted, featuring multiple windows and decorative elements. Surrounding greenery includes trees and blooming flowers, creating a serene outdoor setting. The house is characterized by its soft color palette and well-maintained exterior.

Private room in Canaan

The Stage Coach Lodge Bedroom 2

ValueLocationKitchen

Private room in Rockingham

Visit your Craftsman home away from home-Rm 2 of 2

LocationValueHeating

4.95 out of 5 average rating, 107 reviews

4.94 out of 5 average rating, 52 reviews

A bright living room features a blue sectional sofa adorned with decorative pillows. A wooden bench serves as a coffee table, and a rocking chair is positioned nearby. Large windows allow natural light to fill the space, with light blue striped walls adding a charming touch.

Private room in Randolph

Farm Stay in Antique Farmhouse

LocationBathroomSkiing

Private room in Weathersfield

Beach room in Vermont!

FamilyValueLaundry

4.99 out of 5 average rating, 97 reviews

5.0 out of 5 average rating, 5 reviews

A spacious room features a King bed with white linens, flanked by two bedside tables with lamps. A decorative area rug and a bench are placed at the foot of the bed. Natural light enters through large windows, illuminating the neutral tones of the decor.

Private room in Dover

Classic King in Historic Inn on 32 acres, rm 6

LocationValueDecor

5.0 out of 5 average rating, 4 reviews

A cozy queen room features a wooden bed with a plaid blanket. Two artworks hang on the teal wall, complemented by matching wooden nightstands. Soft lighting is provided by a lamp on one side, while natural light enters through an unseen window.

Private room in Newfane

Queen bed + private bath, breakfast included

LocationOutdoor spacesBathroom

Shared room in Dorchester

Yoga Room - Streeter Mountain Farm

ValueFamilyBreakfast

4.76 out of 5 average rating, 102 reviews

Private room in Woodstock

A simple bedroom features a queen bed with a light-colored quilt. The headboard is crafted from woven material. Bright blue walls are complemented by an orange decorative piece overhead. Bedside tables with lamps flank the bed, and a potted plant adds a touch of greenery.

TETE: Modern design in the heart of the village

ValueLocationParking

4.93 out of 5 average rating, 15 reviews

Bed and breakfast rentals with breakfast

The historic Follansbee Inn is framed by lush greenery and colorful flower beds. A welcoming porch with white railings and a swing invites relaxation. The building features multiple stories and large windows, highlighting its charming architecture in a tranquil setting.

Bed and breakfast in Sutton

Follansbee Inn on Kezar Lake

FamilyBikingComfort

5.0 out of 5 average rating, 4 reviews

Private room in Middlebury

A historic farmhouse is set among lush greenery, featuring a classic facade with large windows. A tree adds shade in the foreground, while vibrant flower beds line the pathway leading to the entrance. The surroundings convey a peaceful rural setting.

Spacious private bed and bath

LocationFamilyHospitality

4.97 out of 5 average rating, 276 reviews

Private room in Killington

The exterior of the farmhouse showcases a spacious, two-story building with a dark roof, nestled among lush green lawns and surrounded by colorful fall foliage. Rolling hills and mountains provide a scenic backdrop, highlighting the natural beauty of the Vermont landscape.

King Room with Private Bath - The Trailside Inn

LocationValueTV

4.94 out of 5 average rating, 141 reviews

4.91 out of 5 average rating, 94 reviews

The historic 1840 property features a white exterior with black shutters and arched windows. An American flag is displayed prominently. The well-maintained lawn is adorned with fallen autumn leaves, and a covered porch is visible, inviting guests to enjoy the scenic surroundings.

Private room in Barnard

The Fan House Vermont Country Home

ValueFamilySkiing

Private room in Weathersfield

The exterior of a vibrant red building is displayed, featuring multiple stories and architectural details such as white trim. Snow covers the surrounding ground, and a light dusting is present on the roof. A paved driveway leads to a parked vehicle, and a whimsical yellow structure adds a pop of color.

The Oak Room - Ladoga

FamilyLocationParks

4.94 out of 5 average rating, 63 reviews

4.89 out of 5 average rating, 93 reviews

The historic Windsor Mansion is situated atop a gentle hill, surrounded by lush greenery and trees in various shades of green. The white exterior of the mansion stands out against the natural backdrop, with many windows reflecting the sky above.

Private room in Windsor

Stay at the largest Colonial Revival Mansion in US

LocationFamilyParking

Private room in Starksboro

A comfortable living room is featured, with a plush sofa adorned with decorative cushions. A small coffee table stands on a patterned area rug, and framed artwork decorates the light blue walls. Natural light enters through large windows, complemented by sheer curtains.

Creek-Side Farmhouse Near Burlington, Vermont

LocationFamilyComfort

4.97 out of 5 average rating, 66 reviews

5.0 out of 5 average rating, 18 reviews

The charming farmhouse features a two-story design with white siding and red shutters, framed by vibrant autumn foliage. A welcoming front door is accented with a seasonal wreath, and a well-maintained front yard with colorful plants is visible, inviting guests to explore.

Private room in Roxbury

Johnnycake Flats Inn, Train Room

LocationHospitalityView

Bed and breakfast rentals with a patio

5.0 out of 5 average rating, 44 reviews

A spacious bedroom features a four-poster bed dressed in white linens and plush pillows. Two bedside tables with lamps flank the bed. A round mirror hangs above a chair beside a small table, while a plush area rug lies underfoot. Windows are adorned with drapes.

Private room in Chester

Farm at Williams River House - Essex Suite

FamilyLocationHospitality

Private room in Barre Town

A cozy room features a white metal bed with a comfortable mattress and soft bedding. Two bedside lamps are placed on white nightstands beside the bed. A ceiling fan provides ventilation, and the room is illuminated by natural light from a large window facing the outdoors.

Horace’s Room

FamilyValueBathroom

4.95 out of 5 average rating, 22 reviews

Private room in Waitsfield

The room features two full beds, each adorned with plaid patterned blankets. A small wooden table is positioned between the beds, beside a lamp, enhancing the cozy atmosphere. Natural light enters through a window with blinds, and a decorative wreath adorns the wall.

The Clayton Room at the Waitsfield Inn.

LocationCleanlinessComfort

4.71 out of 5 average rating, 7 reviews

Private room in Northfield

A charming two-story gray house is showcased with a blue front door and a seasonal wreath. The wrap-around porch features white columns and railings, while landscaped gardens with flower beds enhance the exterior. Adjacent parking and nearby greenery contribute to a welcoming atmosphere.

Charming Inn room 3/6 (Travelers room)

LocationAccuracyIndoor spaces

5.0 out of 5 average rating, 13 reviews

5.0 out of 5 average rating, 69 reviews

A view of a rural landscape featuring vibrant fall foliage in shades of orange, red, and yellow. A farmhouse and several smaller buildings are nestled among the trees, with a winding road leading to them. Rolling hills create a picturesque backdrop.

Private room in Alstead

Country Bed & Breakfast, Sugar Maple Room

LocationFamilyQuiet

4.93 out of 5 average rating, 27 reviews

A historic B&B is nestled among trees, showcasing a classic two-story white exterior with black shutters. The home features a welcoming front porch and manicured landscaping, providing a serene setting. A hint of colorful flowers can be seen in the foreground.

Private room in Antrim

The Historic Copper Pot B&B

ValueFamilyBackyard

A spacious bedroom is equipped with a large bed, two comfortable armchairs, and a decorative fireplace. Natural light enters through multiple windows adorned with curtains, and a vanity area is included. Wood flooring adds character to the warm, inviting space.

Private room in Weathersfield

"Weathersfield Inn" Rustic Inn Taftsville