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, 397 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, 241 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.

Superhost

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, 376 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, 272 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.

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, 651 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

The entrance to the Carriage House is framed by a vibrant red door and a side panel featuring a small square window. A bright yellow mum plant and a pumpkin are placed on a stone pathway leading to the door.

Guesthouse in Chester

4.92 out of 5 average rating, 179 reviews

Historic Carriage House-20 Min to Okemo-Magic MTN

Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

Guest favorite

Place to stay in Town of Rockingham

4.91 out of 5 average rating, 77 reviews

Romantically Cheerful Country Cottage apt.

Welcome to historic, Bellows Falls. This private, romantic escape apartment is the ideal spot to relax, go antiquing, or to launch your amazing ski adventure. Walkable location to town or to a lovely wooded hike. A fully apportioned large kitchen with toaster and microwave gives you control of your meals. An electric fireplace keeps the space cozy and beautiful. We’ll provide basic breakfast essentials, eggs (if the chickens are laying), butter, breads, milk, fruit, etc..

Guest favorite

A wooden structure with a steeply pitched roof is surrounded by lush green foliage. A light-colored pathway leads from the house to the entrance, integrating the building with the natural environment.

Tiny home in Athens

4.9 out of 5 average rating, 123 reviews

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.

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, 277 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 cozy seating area is arranged around a stone firepit, featuring four green Adirondack chairs. The cottage stands nearby, its large windows reflecting the surrounding trees. Scattered pumpkins add a touch of seasonal charm, while twinkling string lights overhead create an inviting ambiance.

Tiny home in Putney

4.94 out of 5 average rating, 754 reviews

Honeycrisp Cottage - A Tiny Timber Frame

Honeycrisp Cottage a Tiny Timber Frame is a bright, energy-efficient dwelling nestled on 9 acres overlooking a beautiful forested mountain & trails to explore along a brook. A peaceful getaway retreat equipped with a living room, a king bed, a loft with a queen bed, a full kitchen, & a full bathroom. *Please No Smoking On The Property Mt. Snow - 50 mins Okemo - 50 mins Stratton - 1 hr Killington - 1 hr 20 mins

Top guest favorite

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.

Barn in Town of Rockingham

5 out of 5 average rating, 14 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)

Guest favorite

A private balcony is showcased with a woven chair and a small ottoman. Hanging flower baskets add color, while the surrounding windows offer a view of the trees and nearby buildings, providing a serene outdoor space for relaxation.

Apartment in Claremont

4.89 out of 5 average rating, 155 reviews

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.