Vacation rentals in Alstead

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Top-rated vacation rentals in Alstead

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Top guest favorite

The exterior of Boulder House is presented, showcasing a modern black facade with large windows. A spacious deck is visible, furnished with two chaise lounges and chairs. Surrounding boulders and colorful fall foliage create a natural and inviting environment.

Cabin in Stoddard

4.98 out of 5 average rating, 103 reviews

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

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, 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, 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 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, 139 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).

Top guest favorite

The image captures a serene landscape with lush green grass and a large tree's shadow. In the background, two farm buildings are visible alongside a field with tall grass, under a soft pastel sky at dusk.

Guest suite in Westminster

4.96 out of 5 average rating, 55 reviews

COZY FARMHOUSE SUITE

Take it easy at this unique and tranquil getaway nestled in a revolutionary historically significant village. You can experience farm living while still close to Rte 91, an Amtrak station and the Connecticut river for fun water activities. This recently renovated studio has a private entrance with parking right outside. Fully equipped kitchen. Bathroom with tiled shower stall, easily accessible. The beautiful sleeping nook is perfect for two. Adorable sitting and dining/work areas.

Guest favorite

The interior features a vaulted wooden ceiling with exposed beams, providing a warm, rustic feel. A ceiling fan hangs from the center, and light fixtures enhance the space. Two framed prints of trees adorn the walls, contributing to the serene atmosphere of the tiny cabin.

Treehouse in Alstead

5 out of 5 average rating, 21 reviews

Owls Nest Treehouse

Brand new tiny cabin retreat. 30 minutes from Keene, and 20 minutes from Bellows Falls, VT., this Owl's Nest is tucked away in a privately-owned forest surrounded by nature on a small farm. Kitchenette, rainfall shower, full Wi-Fi, TV and Private Hot Tub. Local orchards, Many Ski & Snowmobile options, hidden lakes, the Connecticut River, shopping, or a farm-to-table meal, there are activities of every kind just a few minutes away. Only sleeps 2, no pets, not handicap accessible.

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, 644 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 loft bedroom within an A-frame structure displays a spacious bed with a white comforter and decorative pillows. A patterned rug is placed beneath the bed, and large windows frame scenic views. Soft, natural light filters through the space, enhancing the cozy atmosphere.

Chalet in Stoddard

4.95 out of 5 average rating, 263 reviews

Highland Haus AFrame Lake Access Vintage 70s Charm

Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!

Top guest favorite

Home in Alstead

5 out of 5 average rating, 14 reviews

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

🌲Welcome to Birch Croft!🌲 Escape to 83 acres in New Hampshire, where towering pines, winding hiking trails, and a peaceful stream set the scene for your perfect getaway. This spacious home is designed for gathering—whether it's a family reunion, a getaway with friends, or simply a chance to disconnect and recharge. Beds include: 1 king suite, 1 king bedroom, 1 queen bedroom, 2 twin beds, and 4 sleeper sofas.

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)

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Popular amenities for Alstead vacation rentals

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Other great vacation rentals in Alstead

Guest favorite

A vibrant display of flowers in various pots adorns a wooden deck, creating a welcoming entrance. In the background, a lush green pasture extends into the distance, dotted with trees and clearings. A parked vehicle is visible nearby, blending into the tranquil natural setting.

Bungalow in Putney

4.94 out of 5 average rating, 34 reviews

Cozy paradise in Westminster West

JeromeRating, 5 stars9 months ago

I had the pleasure of staying at Hilary’s beautiful home in Putney, Vermont, for a very special occasion—the birth of my daughter. This home was the perfect place for her first days on Earth. The peaceful solitude and tranquil surroundings made it an ideal environment for welcoming new life. The house itself was impeccably equipped with everything we could possibly need. The attention to detail was evident in every corner, making our stay comfortable and stress-free. Hilary was an outstanding host, always responsive and communicative, ensuring we had everything we needed during our stay. The calm, serene environment offered a perfect retreat from the world, allowing us to focus on family and enjoy the beauty of nature. I couldn’t have imagined a better place to begin this new chapter of our lives. I highly recommend Hilary’s home for anyone seeking both comfort and a peaceful, restorative atmosphere.

Superhost

The sleeping area showcases wooden walls and a vaulted ceiling. A spacious bed is positioned across from a lofted bed, accessed by a wooden ladder. Natural light enters through a large window, creating an open and bright atmosphere in the rustic cabin.

Farm stay in Chester

4.85 out of 5 average rating, 81 reviews

Rivers Edge Farm’s Cozy Cabin

KyleRating, 5 stars5 months ago

Jessica was a great host and helped us out with some car troubles. The cabin is very nice and clean and has everything you will need for an affordable price. There is ski resorts and outdoor activities within short distances. I recommend this place and if we are in the area we will stay again.

Top guest favorite

A spacious bedroom features two twin beds with floral-patterned pillows and a matching blue headboard. A bedside table with a lamp is situated between the beds. Natural light enters through a window adorned with light curtains, illuminating the warm wood flooring.

Home in Walpole

4.99 out of 5 average rating, 75 reviews

Charming, Large House in Walpole NH /VT. Border

ReneeRating, 5 stars3 weeks ago

The house was beyond what I expected, it was beautiful, & charming. It was quiet & relaxing. My family went for a weekend wedding but I would rebook for a week. I loved it

Guest favorite

A warm wood-paneled interior features a cozy seating area with a bench and a rocking chair. Large windows provide views of the surrounding forest, while a patterned area rug and a vintage lamp add to the rustic charm.

Cabin in Brookline

4.94 out of 5 average rating, 17 reviews

Off-the-Grid Cabin in the Forest

AndrewRating, 5 stars2 weeks ago

Ideal cabin in the woods for a secluded forest getaway - well stocked kitchen, and the outhouse is 10/10. Very responsive and helpful!

Guest favorite

A comfortable leather sofa is positioned on a screened porch, surrounded by large windows that offer views of the outdoors. A cozy blue pillow is placed on the sofa, and a wooden table with a decorative plant is visible nearby, providing a serene setting for relaxation.

Home in Alstead

5 out of 5 average rating, 14 reviews

Lake Living: Cozy Cove Cottage

LisaRating, 5 stars9 months ago

We loved this little lake community on peaceful Lake Warren. This newly renovated house worked well for us and family. The dock had a beautiful view and there were 2 screened in porches to spread out in good weather. There was a surprise cold snap and the owners immediately dropped off extra heaters. We felt well taken care of and would love to return. (The stairs to 2 upstairs bedrooms were steep. Be careful of you’re wearing socks.)

An interior view showcases a wooden staircase leading to a lofted area, framed by warm wood paneling. A comfortable yellow chair sits beside a small television on a vintage dresser. Natural light flows through large windows, illuminating the open floor plan adorned with eclectic art.

Cabin in Alstead

4.82 out of 5 average rating, 11 reviews

Rustic Artsy Cabin in the Woods

RachelRating, 5 stars7 months ago

We absolutely loved our stay at Diana’s place! The location was perfect for our needs. The location was absolutely gorgeous. Our dogs loved taking walks on the dirt roads, and we all loved cozying up on chilly evenings in front of the wood stove. The beds were comfortable and on cold nights we were pleasantly surprised at how warm the stove kept the space. Diana was extremely communicative and helpful, while things were well labeled and easy to figure out, we had a great experience with the caretaker, Ashley, going above and beyond to bring us an item we had asked about. I cannot say enough good things! As a former local - you could not find a better space in this area.

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.

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Vacation rentals in Alstead

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