Vacation rentals in Town of Rockingham

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Top-rated vacation rentals in Town of Rockingham

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Top guest favorite

A welcoming porch is presented, featuring a combination of seating options including a cushioned chair, a rocking chair, and a white wicker chair. Wooden steps lead up to double glass doors framed by warm wood panels, inviting guests into the space.

Home in Putney

4.94 out of 5 average rating, 394 reviews

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.

Guest favorite

An iron bridge spans a flowing river, supported by multiple stone pillars. Waters cascade over large rocks in the foreground, creating a natural landscape. The setting sun casts a warm glow, highlighting the textures of the bridge and the surrounding flora.

Apartment in Bellows Falls

4.94 out of 5 average rating, 238 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.

Guest favorite

A private boat is seen docked at a wooden pier, surrounded by lush greenery. The calm river reflects the surrounding trees, creating a serene scene. Light filters through the foliage, enhancing the peaceful atmosphere of the waterfront.

Guesthouse in Springfield

4.85 out of 5 average rating, 373 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.

Superhost

A bathtub is positioned beside a large window, offering views of the surrounding greenery. Natural light filters through sheer curtains, illuminating the tub and a neatly rolled towel placed nearby.

Cottage in Putney

4.82 out of 5 average rating, 271 reviews

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.

Guest favorite

A snow-covered mountain is visible in the distance, with skiing trails marked by white lines. Soft clouds drift across the peak, bathed in the warm colors of sunset. Surrounding trees are silhouetted in front of the mountain, adding depth to the natural landscape.

Tiny home in Jamaica

4.94 out of 5 average rating, 1,266 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Top guest favorite

A wooden chicken coop is visible, featuring a rustic design with a small door and decorative elements. A fenced area surrounds the coop, offering a view of plants and a bright yellow chicken statue. Lush greenery and trees provide a natural backdrop.

Barn in Chester

4.99 out of 5 average rating, 639 reviews

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.

Guest favorite

A spacious kitchen area features wooden cabinetry and a large butcher block countertop. A stainless steel sink is situated beneath a window, while shelves hold kitchen essentials. A striped area rug adds warmth to the hardwood floor, and a pendant light provides gentle illumination.

Apartment in Town of Rockingham

4.95 out of 5 average rating, 274 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.

Guest favorite

A comfortable outdoor seating area is featured on a wooden deck. Wicker furniture, including a sofa and chairs, is arranged around a coffee table. An umbrella provides shade, while lanterns are positioned on the ground. Lush greenery surrounds the space, contributing to a serene atmosphere.

Cottage in Chester

4.89 out of 5 average rating, 94 reviews

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!

Superhost

A compact bathroom features light-colored tiled flooring and neutral-toned walls. A shower curtain with blue stripes encloses the shower area. A small vanity with a sink and mirror is positioned beside a toilet, while a decorative stool and neatly arranged towels complete the space.

Home in Town of Rockingham

4.69 out of 5 average rating, 42 reviews

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

Please read the whole listing. My place isn’t perfect. Simple cottage in Bellows Falls VT. 70mins to Killington, 45mins to Okemo & Mt Snow. Cute town, with lots of hiking and biking nearby. Recent renovation, and far from perfect house. However, I’m priced fairly. All Airbnb money received accelerates the list of house projects. Feel free to reach out with any questions before you book.

Guest favorite

A wooden deck features a set of steps leading to a private entrance, surrounded by freshly fallen snow. The exterior is painted deep blue with red-trimmed windows, complementing the serene rural setting.

Barn in Town of Rockingham

5 out of 5 average rating, 11 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)

Top guest favorite

A wooden deck features a small round table and two folding chairs, overlooking vibrant autumn foliage and a distant sunset. The landscape stretches across a valley, showcasing a blend of trees with colorful leaves against a backdrop of rolling hills.

Apartment in Andover

4.98 out of 5 average rating, 428 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Superhost

An open living space features a wooden countertop with a microwave and decoratively arranged plants. The wall is adorned with a collection of framed images, while the area is softly illuminated by a ceiling light. Nearby, a dining table with wooden chairs offers seating.

Apartment in Town of Rockingham

4.83 out of 5 average rating, 185 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.