Vacation rentals in Rockingham

Guesthouse in Town of Rockingham

A vibrant garden is displayed, featuring a variety of blooming flowers in shades of pink and white. Lush greenery surrounds the garden, with tall trees in the background. The scene is bathed in natural sunlight, creating a peaceful outdoor setting.

4.89 out of 5 average rating, 44 reviews

Peaceful Historic Cottage

Picturesque private two bedroom cottage attached to historic estate, located within the village of Saxtons River. Walking distance to the quaint downtown, Vermont Academy and an extensive network of hiking trails. Short drive to several Southern Vermont attractions including Okemo and the Vermont Country Store. The grounds boast 6 acres of sprawling gardens, an orchard and fire pit perfect for star gazing. Experience this special property which has been owned by the same family for 200 years.

4.93 out of 5 average rating, 406 reviews

A rustic building with wooden siding is partially surrounded by a foggy landscape. An elevated deck with rocking chairs invites relaxation. The entrance features glass doors flanked by large windows, allowing natural light to illuminate the interior. Surrounding greenery creates a serene atmosphere.

Home in Putney

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

A billiards room features a red pool table with cues and balls arranged on it. Large windows allow natural light to fill the space. Bar stools are positioned at a small pub table, and warm-colored curtains frame the windows.

4.94 out of 5 average rating, 248 reviews

Village Flat with Antique Billiards

Charming and spacious first floor, 3 Bedroom, 1 Full Bath apartment. Sleeps 5 (1 King, 1 Queen and 1 twin). It is nestled in the center of the Bellows Falls village, a short 5-minute walk to downtown, where you will find great little shops and eateries. We are centrally located in Southern Vermont ~ 40 min from several ski areas (Okemo, Magic, Bromley, Stratton, etc.) about one hour from Killington Resort, Mount Snow, and Mount Sunapee (NH), and ~ 20 mins from Brattleboro, VT, or Keene, NH.

Guesthouse in Springfield

An aerial view captures a cozy cottage situated along the Connecticut River. Lush greenery borders the water, and a small pathway leads to the cottage. A boat glides along the river, highlighting the serene setting surrounded by forests and rolling hills.

4.84 out of 5 average rating, 380 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

4.82 out of 5 average rating, 276 reviews

The exterior of a wooden cabin is displayed amidst a snowy landscape. The structure features a sloped roof with skylights and a covered entrance that offers protection from the elements. A vehicle is parked nearby, and snow covers the ground and surrounding trees.

Cottage in Putney

The Cottage, a house built for guests.

In the village there is a wonderful farm to table restaurant, the Gleanery. A local pub, friendly, great food with indoor and outdoor dining & pub. The General Store, is the oldest continually run general store in Vt. The Next Stage, Yellow Barn, Sandglass Theater, these places provide an amazing collection of visual, musical, spoken word and world renowned art and artist to experience. These cultural event locations are but a mile away for the Cottage I hope you choose for your stay.

4.99 out of 5 average rating, 666 reviews

A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.

Barn in Chester

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

4.91 out of 5 average rating, 133 reviews

A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.

Tiny home in Athens

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

A spacious studio is depicted, featuring a cozy seating area with a blue couch and a patterned loveseat. A large wooden dining table is positioned nearby. The room is accented by vibrant artwork and is illuminated by natural light from two windows, complementing the warm wood flooring.

4.94 out of 5 average rating, 285 reviews

Stunning Studio in historic Downtown Bellows Falls

Beautifully curated and spacious studio located in historic downtown Bellows Falls, VT. Come to escape the hustle and bustle of a big city without giving up metropolitan amenities. With a great location, you can walk to the train station, local bars and restaurants, shops, movie theater, etc. From the studio, you are a short distance drive to many outdoor activities that Vermont has to offer such as hiking, kayaking, mountain biking, etc.

4.9 out of 5 average rating, 102 reviews

The exterior of an 1840s stone house is displayed, featuring a warm red door and large windows under a sloping roof. A well-maintained garden surrounds the entrance, and a tall tree provides shade. A gravel path leads to the house, with a visible stone wall along the yard.

Cottage in Chester

Quaint stone house!

⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!

Barn in Town of Rockingham

A view from a deck presents a lush green yard, framed by trees and rolling hills in the background. The expansive grass lawn gently slopes downward, and a solitary tree stands prominently on the left, set against an overcast sky.

5 out of 5 average rating, 18 reviews

Quiet Country Retreat

New construction. Private space in a tranquil rural setting. Large kitchen, living area and outdoor deck space. Easy access from Interstate 91 in beautiful southern Vermont. Perfect for a solo or couples getaway. Nearby attractions: The Vermont Country Store (2 miles) Rockingham Meeting House (1 mile) Downtown Bellows Falls (6 miles) Main Street Chester (9 miles) Okemo Mountain (22 miles)

4.89 out of 5 average rating, 160 reviews

A spacious bedroom features a large bed with a decorative canopy and plush pillows. Soft lighting from a chandelier enhances the room's ambiance. A patterned carpet covers the floor, while elegant curtains frame the windows, and a cozy seating area includes a small side table.

Apartment in Claremont

Beautiful 1 bedroom apartment with balcony

Bienvenue chez nous! Experience comfort and modern beauty in this completely renovated apartment attached to a historic Victorian home. The one bedroom apartment has a private bathroom and your own balcony to enjoy. Close to popular skiing areas of Mt Sunapee (20 minutes) and Okemo (35 minutes), in addition to enjoying local hiking and cycling at Mt Ascutney, Moody Park, and Arrowhead.

A bedroom features green walls, with large windows dressed in light curtains allowing natural light to filter through. A wooden bed with white bedding is positioned near a yellow dresser. Two comfortable armchairs are provided, complemented by a floor lamp for additional lighting.

4.83 out of 5 average rating, 191 reviews

Apartment on Main Street

One bedroom apartment with kitchenette (mini-fridge, coffee maker, microwave, dishes etc.), full bathroom with laundry, and open living space. I am an English teacher, so there are lots of books! Apartment is located in the Village of Saxtons River- within easy walking distance from the Market, Vermont Academy, our new Park, and Main Street Arts.

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Other great vacation rentals in Rockingham

5 out of 5 average rating, 9 reviews

The living room features a large sectional sofa positioned toward a TV stand, providing ample seating. A ceiling fan is installed above, and large windows allow natural light to fill the space. A coffee table rests in the center, while a dining area is visible through an adjacent room.

Home in Chester

Bright and spacious 3 bed/3 bath

A rustic cabin exterior is presented, featuring a wooden facade with a green metal roof. A small porch with seating is visible, along with a snow-covered landscape and surrounding trees, contributing to a serene natural setting.

Farm stay in Grafton

4.72 out of 5 average rating, 65 reviews

Cabin2

5 out of 5 average rating, 14 reviews

A modern timber frame cabin is set on a green lawn surrounded by trees. The front porch features two chairs and a welcoming entry, with large windows allowing natural light to enter. The wood exterior complements the serene woodland environment.

Cabin in Townshend

Timber Frame Home on 5 Private Acres

5 out of 5 average rating, 57 reviews

A serene outdoor setting is captured, featuring a colorful hammock suspended between two large trees. Surrounding foliage showcases autumn colors, with a carpet of fallen leaves covering the ground. Rolling hills in the background contribute to the tranquil landscape.

Cabin in Springfield

East View Farm Retreat Cabin

5 out of 5 average rating, 6 reviews

A bright bedroom features light blue walls and a spacious bed with a floral bedspread. A wooden desk and chair are positioned near a window, which offers natural light. Plush carpet and elegant drapery complement the cozy atmosphere.

Apartment in Springfield

Sunny, serene, second floor

5 out of 5 average rating, 9 reviews

A charming restored house with a distinctive pink exterior is framed by lush greenery. The front door is painted a vibrant teal, complementing the white trim and windows. A tall tree stands beside the home, adding to the serene outdoor setting.

Home in Grafton

*NEW* The Pettengill Schoolhaus- bike to village

A living room is displayed featuring a comfortable couch and two armchairs arranged around a coffee table. A bookshelf is visible along one wall, and a television is placed nearby. Natural light filters through the windows, adorned with dark curtains, highlighting the wooden floor.

Home in Town of Rockingham

4.66 out of 5 average rating, 50 reviews

Simple 2+ bed, no frills, all necessities covered!

A charming outdoor area features a white pergola surrounded by lush greenery and flowering plants. Two chairs are placed on a patio, offering a serene setting. A pop of color is provided by hanging planters and a vibrant red door, complementing the natural surroundings.