Holiday rentals in Town of Rockingham

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Top-rated holiday rentals in Town of Rockingham

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Top guest favourite

Home in Putney

4.94 out of 5 average rating, 396 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 favourite

Flat 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.

Guest favourite

Guest house 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

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.

Top guest favourite

Barn in Chester

4.99 out of 5 average rating, 648 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 favourite

Guest house 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 favourite

Tiny home in Athens

4.9 out of 5 average rating, 122 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 favourite

Flat in Town of Rockingham

4.95 out of 5 average rating, 276 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 favourite

Tiny home in Putney

4.94 out of 5 average rating, 753 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 favourite

Barn in Town of Rockingham

5 out of 5 average rating, 13 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 favourite

Flat in Claremont

4.89 out of 5 average rating, 154 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.

Top guest favourite

Flat in Andover

4.98 out of 5 average rating, 430 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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Other great holiday rentals in Town of Rockingham

Guest favourite

Flat in Grafton

4.83 out of 5 average rating, 12 reviews

Grafton Homestead, Grafton, VT

WaydeRating, 5 stars1 week ago

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!

Cabin in Townshend

5 out of 5 average rating, 4 reviews

Timber Frame Home on 5 Private Acres

KatyaRating, 5 stars1 week ago

We loved our stay at the house. It is brand new, extremely clean, very well equipped, and surrounded by beautiful nature. Definitely at the top of the list of the (many) AirBNBs we have stayed at. The coffee station was a lovely touch, and we appreciated having organic coffee from a small local roaster. The mattress was firm and comfortable - something that tends to be difficult to come by at rental properties. And (important for us, city people) - we couldn't hear cars anywhere at all. The property is very private, rural, secluded, and peaceful. Thanks for hosting us and we hope to be able to escape here again!

Guest favourite

Home in Chester

4.88 out of 5 average rating, 41 reviews

Historic 150-Year-Old Farmhouse | Jacuzzi included

CarlyRating, 5 stars2 weeks ago

This was truly an oasis for me and my family during our stay in beautiful Vermont. Collin was an excellent host and was accommodating during my entire stay. It is a large beautiful farm house with the antique charm but updated amenities. My children enjoyed the hot tub and the large outdoor area while I had the space to cook some excellent meals. The town is just lovely with friendly people everywhere you go. I highly recommend Smitty’s for a local small grocery store. Our host Collin even gave us a gift card to a local pizza place that is superb. I will certainly stay again!

Top guest favourite

Home in Springfield

5 out of 5 average rating, 28 reviews

Scandinavian Serenity Close to Okemo

TodRating, 5 stars4 days ago

Yulia and Mark's place is perfect for a getaway, so perfect in fact that it takes a little while to sink in. Located on a forested hill, the pristine mid-century modern house is quiet, calm, and restorative. Little by little, lovely details accumulate - like the glorious landscaping, the harmony of sloping roofs on outbuildings in synchrony with the bold and simple lines of the main house, the view of tall trees from each room - including bathrooms, the total quiet since the road nearby is hardly traveled. The place is full of lovely amenities and the sauna is a delight - even in heat and easy to use. Mark and Yulia were both quick to communicate and to help solve small problems, and we were lucky to meet Mark in person - wonderful and welcoming. We only wish we could have stayed longer. Next time...soon, I hope!

Flat in Springfield

5 out of 5 average rating, 4 reviews

Sunny, serene, second floor

EvaRating, 5 stars2 weeks 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 favourite

Home in Alstead

5 out of 5 average rating, 15 reviews

83-Acre Getaway: Hot Tub, Pool Table, HikingTrails

MarshaRating, 5 stars2 weeks ago

Outstanding!! Birch Croft is truly exceptional. We enjoyed all the space inside and out -including two kitchens, a huge game room, quiet nooks to sit and read from the extensive library, a large front porch, spacious bedrooms, a fire pit and of course the absolutely gorgeous 83 acres that surrounded us. We saw three deer and a fox, and took a walk on the trail. Nate was the perfect host-responsive, helpful and courteous-and we appreciated all that he and Olivia have done to make this place so special. Loved the historic vibe, the art and decor, and the very well stocked kitchen (we made dinner for 13 and had everything we needed from silverware to gadgets). DO NOT HESITATE to book here-this is a place to make memories for sure and we look forward to returning again soon.

Guest favourite

Flat in Town of Rockingham

4.97 out of 5 average rating, 87 reviews

Cozy studio at Leslie's Tavern in Rockingham

JoelleRating, 5 stars3 days ago

We loved our stay at Leslie's Airbnb. I would go back in a heartbeat. The loft is very cozy and well decorated. All you need is in there and if you need anything else, the owners are very responsive and so nice! We felt in love with the owners ♡. It is hard to beat their hospitality. During your stay, I recommend you trying the restaurant, great food and service.

Guest favourite