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, 395 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, 239 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, 374 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 night sky displays a gradient of purple and dark blue tones, with stars scattered across the expanse. Silhouettes of power lines extend from the foreground into the distance, contrasting against the celestial backdrop.

Camper/RV in Guilford

4.93 out of 5 average rating, 141 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

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, 1,269 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, 645 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

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 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, 275 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.

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

4.63 out of 5 average rating, 43 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.

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, 12 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 offers a peaceful view of rolling hills during sunset, with vibrant autumn foliage on either side. A small round table and two folding chairs are positioned for outdoor relaxation, inviting moments of tranquility while enjoying the natural surroundings.

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!

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Popular amenities for Town of Rockingham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Town of Rockingham

Guest favorite

A calm river meanders through lush greenery, framed by vibrant wildflowers along the bank. The water reflects the surrounding trees, which provide a natural canopy. Sunlight filters through leaves, creating a serene atmosphere that invites relaxation in the beautiful outdoors.

Apartment in Grafton

4.83 out of 5 average rating, 12 reviews

Grafton Homestead, Grafton, VT

WaydeRating, 5 starstoday

Draa’s space was cute, clean, and well-cared for. It was the perfect spot for us to enjoy our friend’s nearby Grafton wedding and other VT locales. Hosts’ directions were clear, and they provided great ideas to explore surrounding areas. Thanks again!

Guest favorite

Tiny home in Chester

4.93 out of 5 average rating, 40 reviews

Sage House at Camp Greenwood Vermont with Sauna

PatrickRating, 5 stars1 week ago

Was exactly like the photos. A beautiful home and beautiful town.

A light blue bathroom features a vintage-style pedestal sink and a full-size washing machine. A decorative wall mirror enhances the space. Natural light filters through the doorway, revealing a soft patterned floor tile and a clear shelving unit against the wall.

Apartment in Springfield

5 out of 5 average rating, 4 reviews

Sunny, serene, second floor

EvaRating, 5 stars1 week ago

What a blissful place to stay. The apartment was spotless, cozy, and incredibly comfortable. The linens were crisp and fresh, and the bathroom towels were some of the thickest, most luxurious I’ve ever experienced in an Airbnb. The decor is fresh and modern with a playful retro touch in the kitchen that adds charm and character. I wish I had more time to enjoy the space—especially the perfect work-from-"home" setup tucked under the eaves. I was attending an artist retreat at the Smiley Manse, which was conveniently less than five minutes away.

Top guest favorite

A cozy interior of a tent camp showcases a plush orange sofa paired with a dark armchair. A rustic wooden coffee table is adorned with a candle and a book. A wood-burning stove provides warmth, while large windows offer views of the outdoor deck.

Tent in Springfield

5 out of 5 average rating, 46 reviews

Highwood Retreat: The East Camp

AleksaRating, 5 stars1 week ago

What a magical place! Katharine was so friendly and had great communication from the moment we booked. The tent was spacious and cozy! You can tell lots of time and detail went into creating such a beautiful space! The bathroom was just a few steps away and was super clean. There were also tons of beautiful hikes and yummy places to eat nearby. We loved everything about this place and our dog was in absolute heaven running around! We’re already talking about visiting again in the winter!

Top guest favorite

Home in Grafton

5 out of 5 average rating, 8 reviews

*NEW* The Pettengill Schoolhaus- bike to village

KpollardochabRating, 5 stars3 months ago

So charming. LOVED everything about this place. Was a perfect meeting spot for two long time friends- one driving in from Maine, the other New Jersey with two college aged kids who drove down from UVM. The place can't be described in words- so quaint, homey, welcoming, amazing location, adorable town. And the responsiveness of the host was so great- throughout the night of a pretty good snowstorm. Will come back again just to stay here!!! Thanks for sharing this gem of a spot with us.

Guest favorite

A modern kitchen area displays a light-colored cabinetry, accented by a wooden countertop. Natural light filters through two windows adorned with sheer curtains, illuminating a sink beside a small potted plant. A wall clock and kitchen essentials are neatly arranged in the space.

Apartment in Town of Rockingham

4.97 out of 5 average rating, 86 reviews

Cozy studio at Leslie's Tavern in Rockingham

LisaRating, 5 stars1 month ago

I believe this was the 4th time I’ve booked this place, which I believe should speak for itself as to how much I enjoy staying at Leslie’s quaint little bungalow.

Top guest favorite

A welcoming entrance features a wooden door, surrounded by stone columns and a sturdy roof. Soft lighting emanates from inside, illuminating a cozy space. The path leads to the entrance, framed by well-maintained landscaping, hinting at the natural surroundings of the cabin.

Cabin in Chester

5 out of 5 average rating, 14 reviews

Luxe Rustic Cabin Near Okemo

PaigeRating, 5 stars2 weeks ago

Ravens Loft was a great place to stay for me and my boyfriends anniversary. Everything was clean and well kept.

A compact interior showcases wooden paneling and an A-frame ceiling. A ladder leads to an upper sleeping area. Shelving displays dinnerware and glassware, while a kitchenette features utensils and appliances. A cozy rug adds warmth to the space, with natural light filtering through a nearby window.

Tiny home in Town of Rockingham

4.77 out of 5 average rating, 101 reviews

Tiny Home w/ Parking - Pet Friendly & Fireplace!

JohnRating, 5 stars1 month ago

Very cute little cottage that is close to walking trails around a reservoir and within walking distance of a great village downtown with shops and restaurants. Sarah was very responsive and helpful. A quiet and comfortable place that is still close to village amenities. Definitely worth the stay.

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Vacation rentals in Town of Rockingham

Top-rated vacation rentals in Town of Rockingham

Vacation rentals for every style

Popular amenities for Town of Rockingham vacation rentals

Other great vacation rentals in Town of Rockingham

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