Kid-friendly vacation rentals in Cheshire County

4.97 out of 5 average rating, 233 reviews

A lush garden landscape is presented, featuring blooming pink azaleas alongside vibrant greenery. A tranquil stream runs through the garden, flanked by an array of flowers and well-maintained grass, surrounded by dense trees, creating a serene natural environment.

Apartment in Dublin

Private Dublin apartment nestled in the woods

Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.

4.96 out of 5 average rating, 181 reviews

A charming wooden cottage is surrounded by trees, featuring a screened-in porch. The exterior showcases warm, natural tones with a combination of shingles and wood paneling. A gravel path leads to the entrance, bordered by vibrant flower beds.

Cabin in Harrisville

Trailside Cottage in charming Harrisville, NH

Hike, bike, cross-country, snowshoe, or just inhale/exhale and enjoy the peace and quiet of a classic New England escape. Welcome to Trailside Cottage, a charming getaway in Harrisville, NH. Recently converted into a cozy space for two. It sits alongside one of the many trails in the Harrisville area, and is accessible to all of the amenities in the Monadnock Region. Our small farm is next door which means you might hear the sounds of country life including our donkey who brays at times!

4.99 out of 5 average rating, 176 reviews

An inviting open living space showcases warm brick walls and original timber beams. A spacious seating area features a brown leather couch and wooden coffee table, while a grand piano occupies one corner. Large windows with serene views of the outdoors offer natural light.

Loft in Peterborough

Peaceful Mill on the Water - Home Away from Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Superhost

The exterior of a wooden cabin is displayed amidst a snowy landscape. The structure features a sloped roof with skylights and a covered entrance that offers protection from the elements. A vehicle is parked nearby, and snow covers the ground and surrounding trees.

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.

4.88 out of 5 average rating, 164 reviews

The compact kitchen features modern appliances, including a microwave and refrigerator, paired with wooden cabinetry and a dining area. Light-colored wood flooring extends throughout, and a staircase leads to the sleeping loft above. Decor elements include framed artwork and a vase of flowers positioned on the counter.

Tiny home in Brattleboro

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

Superhost

A modern kitchen area is equipped with white cabinetry and a black countertop. Essential appliances include a microwave, electric range, and refrigerator. A coffee maker and toaster are also present. The backsplash features a sleek black and white tile design, adding a touch of contemporary style.

4.82 out of 5 average rating, 165 reviews

Lynda's Suite: Seasonal Stays

Welcome to The Phineas Handerson House, originally built in 1827 by the “the happiest man in town” Able Wilder. Modern eclectic one-bedroom apartment, just one block from Central Square in Downtown Keene. Featuring newly remodeled kitchen, fitted with electric range and microwave. Other tenants occupy part of the building, but guests have a private entrance and off-street parking behind the building. Comfortable for two guests but can sleep up to four. Pet friendly!

4.93 out of 5 average rating, 353 reviews

A welcoming living space features two patterned armchairs flanking a coffee table. A desk is positioned against the wall, and natural light enters through a door leading outside. A coat rack is mounted next to the door, and a fire extinguisher is visible on the wall.

Condo in Brattleboro

Private & Quiet Studio Apt. in Vermont

Clean, comfortable , quiet and snug, this studio apartment is a great place to come and relax in. It has a comfy QUEEN size bed with a 40” LCD at its foot, a kitchen set up for cooking and a desk with a view of a green field. This apartment is situated on the ground floor of our detached garage. Our garage sits behind our home, well away from the street. We live in a residential neighborhood that is conveniently located near I91, Route 30, Route 9 and Downtown .

4.95 out of 5 average rating, 264 reviews

An A-frame chalet is illuminated at dusk, showcasing its triangular structure and charming front porch. Warm light spills from the windows, and twinkling string lights enhance the serene outdoor setting surrounded by trees.

Chalet in Stoddard

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!

Guest suite in Fitzwilliam

A bright corner features a small white table flanked by two chairs, positioned beneath a large arched window. The window showcases vibrant autumn foliage in shades of orange and yellow, while soft curtains frame the scene, allowing natural light to fill the space.

4.98 out of 5 average rating, 188 reviews

The Great Room in Historic Fitzwilliam

Come relax in the great room! Large space with full bathroom, beautiful picture windows, spacious closet, and use of deck included. Deck includes a cozy fire pit table, gas grill, and a nice view of the beaver pond, great for bird watching! Please don't hesitate to reach out if you are traveling with children and/or pets, we are often able to accommodate on a case by case basis. Please note stairs are required for entry via the deck entrance.

4.92 out of 5 average rating, 201 reviews

A bright living area features large windows framing views of the outside scenery. A modern entertainment unit holds a large television above a stylish piece of furniture. A soft pouf and a potted plant add warmth and character to the space.

Apartment in Winchester

Downtown Loft next to Distillery

Enjoy a lovely weekend getaway in this cute 1 bedroom loft, centrally located in Winchester, NH. Enjoy a tasting at New England Sweetwater Farm & Distillery next door. This cozy loft features a full kitchen, 3/4 bath as well as a bedroom and living/dining room. 20 minutes to Keene, Brattleboro and Chesterfield. Access to Pisgah State Park, the Ahsuelot Rail Trail and Forest Lake. Come see what our beautiful area has to offer!

A comfortable brown sofa with decorative pillows is positioned near two large windows, allowing natural light to illuminate the space. A small round coffee table is set in front, featuring a decorative vase and magazines, while a potted plant adds a touch of greenery.

4.99 out of 5 average rating, 135 reviews

Sunny New England Apartment

Welcome to Keene. We hope you enjoy your stay with us. We are the top 1’% air bnb reviews in the country. Over the last 7 years we have put everything we can think of to make your stay enjoyable and comfortable. Apartment is on the second floor. You must be able to use stairs. There was a no accommodations for wheel chairs. No smoking anywhere on property. Property is listed by K + M events LLC.

A spacious living area features a large, brown leather sofa positioned around a central area rug. Plants are placed throughout, with a decorative mirror and artwork on the walls. A television is situated on a low table, enhancing the cozy atmosphere.

4.96 out of 5 average rating, 204 reviews

Gorgeous 1-Bedroom Space in Historic Bellows Falls

Enjoy a stylish experience at this centrally-located place. Bellows Falls is a historic village located in Southern Vermont. Once a booming mill town, now a quaint picturesque village with shops, restaurants, and more. The space is located right in the center of town with plenty of space for those seeking to unwind in a small New England village.

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Popular amenities for Cheshire County kid-friendly rentals

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Kid-friendly house rentals

4.94 out of 5 average rating, 54 reviews

Home in Keene

Ultimate Family Vacation Home

Lawrence J.Rating, 5 stars3 weeks ago

My wife and I traveled from Cary, NC to spend the Memorial Day weekend with family. Misha's Airbnb property provided plenty of space as we had four family members also staying at the Airbnb. Highly recommend Misha's Airbnb...looking forward to staying again the next time we visit Sullivan NH.

4.99 out of 5 average rating, 218 reviews

The kitchen features modern stainless steel appliances, including a Viking stove and ample counter space. Exposed brick and wooden beams create a warm atmosphere. A wood stove is positioned nearby, complemented by a rustic brick floor. Natural light filters through the large windows.

Home in Putney

Lovely Brick Schoolhouse

GretchenRating, 5 stars2 weeks ago

The schoolhouse is a lovey, comfortable peace place!

4.89 out of 5 average rating, 19 reviews

A tranquil bedroom features a spacious bed dressed in a light blue coverlet and flanked by two nightstands. A cozy throw is placed at the foot of the bed. Natural light enters through a window adorned with dark blinds, creating a calm atmosphere.

Home in Walpole

A Quaint Setting in the Center of Walpole Village

DeannaRating, 5 stars2 weeks ago

We felt right at home in this cute comfy house in Walpole. We felt like we stayed with family. Very cozy and had everything we needed for our week stay. We will be back!!!

4.89 out of 5 average rating, 104 reviews

The exterior of a two-story wooden home is shown, surrounded by a lush green lawn. A large tree provides shade, while the blue sky features scattered clouds. A relaxed seating area is visible on the grass, enhancing the scenic countryside setting.

Home in Putney

Peaceful Beautiful Mountain Home Spectacular Views

LibbyRating, 5 stars3 months ago

We had a wonderful stay. Very peaceful location and the views are amazing!

4.99 out of 5 average rating, 156 reviews

Home in Keene

Downtown Hot Tub Escape

KylaRating, 5 stars2 weeks ago

We had a great stay here! It was simple and exactly what we needed, we’d definitely stay here again in future trips to Keene!

5 out of 5 average rating, 104 reviews

Sunset is seen through a row of trees along the lake, casting gentle reflections on the water's surface. A boat is visible in the distance, leaving ripples as it moves across the calm lake, while the sky transitions from blue to shades of orange and gold.

Home in Washington

Newer Home on quiet 200 acre lake - sleeps 6

ChrisRating, 5 stars2 weeks ago

This home is beautiful ,well equipped, and the perfect spot to relax. Melora was very friendly and helpful. The little extra touches was what made the home feel so comfortable and the view is just perfect. We are definitely planning a second stay in the near future.

4.95 out of 5 average rating, 145 reviews

A cozy, two-story cape-style home is depicted, featuring green siding and a slate roof. The well-maintained front yard features lush, green grass and manicured flower beds. Two white adirondack chairs are positioned on the lawn, inviting relaxation amid the surrounding trees.

Home in Peterborough

Cozy Cape - close to downtown Peterborough

SharonRating, 5 stars1 week ago

We had a lovely stay at Lori’s cozy cape. Home is very neat, clean and accommodating. We were greeted with a bottle of wine, some bottles of water and biscotti for our morning coffee. Keurig with many varieties of tea and coffee, creamers and sweeteners at the ready. Numerous brochures available, comfortable furniture and we all slept great! Lori is very responsive! Neighborhood is quiet. Will definitely return if ever in Peterborough area again! Thanks for all!

4.95 out of 5 average rating, 341 reviews

A charming gray house is nestled among lush greenery and mature trees. The property features a well-kept lawn with diverse shrubs and plants, offering a serene outdoor environment. Soft sunlight filters through the foliage, creating a peaceful natural setting.

Home in Putney

Cozy Train Depot in Putney Vermont

JudithRating, 5 stars3 weeks ago

Nice one level home. Actually enjoyed the trains. We would go outside when possible to see them. Noise level was low. Easy on and off highway.

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Kid-friendly apartment rentals

A sitting area features a modern black sofa and a round glass coffee table. Soft floor cushions are positioned nearby. Natural light enters through two large windows framed by blue and white striped curtains. A textured wall hanging and artwork adorn the walls.

4.91 out of 5 average rating, 79 reviews

Lovely light-filled 2 bedroom flat

BrendaRating, 5 stars1 day ago

Sweet place. Comfortable, Quiet and safe. Three things I look for!

A charming historic house is presented in a sketch style, featuring a welcoming front entrance with a set of steps leading to the porch. Large windows adorn the front, and the home is surrounded by greenery, conveying a sense of tranquility.

5 out of 5 average rating, 5 reviews

Dover by Downtown

RyanRating, 5 stars2 weeks ago

Nice place. Very clean. Well-stocked. Short walk to downtown Keene with lots of restaurants and breweries. Great communication! Owner even put in a fire pit after I asked if she had one!

Superhost

A bedroom features green walls, with large windows dressed in light curtains allowing natural light to filter through. A wooden bed with white bedding is positioned near a yellow dresser. Two comfortable armchairs are provided, complemented by a floor lamp for additional lighting.

4.83 out of 5 average rating, 186 reviews

Apartment on Main Street

CraigRating, 5 stars1 month ago

We have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.

4.97 out of 5 average rating, 97 reviews

A spacious living area features a comfortable, light-colored sofa with multiple cushions. A low, dark wooden coffee table is centered on a textured rug. Green plants are positioned throughout, and ample natural light enters through large windows adorned with simple treatments.

Apartment in Putney

Minimal organic hideaway inspired by nature

ItaRating, 5 stars3 weeks ago

Katherine’s space was so cozy! It was exactly what I needed for a retreat from daily life. I found both the loft and the daybed very comfortable. There were dimmers on most of the light fixtures, which was important to me because I like low-light settings. The kitchen included a counter with stools and was really quite beautiful. This Airbnb was within walking distance to a local restaurant, the general store and a food co-op. I decided not to rent a car because I was there for R&R., however , if you had a car, just a few minutes outside of town you would see beautiful trees all with leaves in there spring splendor. You could get to Brattleboro in about 20 minutes if you’re looking for more choices of restaurants.. (I decided to take the train up so I took a taxi to the Airbnb from the train and back to the train at the end of my trip.). Although it rained most of the time I was there, it was perfect for my goal of R&R.

A spacious living area features a comfortable brown leather sofa and a dining table with seating for four. The open layout emphasizes natural light, with a loft area visible above. A map hangs on the wall, adding a touch of character to the modern decor.

5 out of 5 average rating, 21 reviews

The Darling Suite

GarnerRating, 5 stars1 day ago

The space was newly renovated. There was intricate trim molding around the doors. The grey hardwood floors gave a a contemporary vibe mixed with the historic see through floor in the kitchen. The patio in the back was spacious and had a gas grill. The area was quiet at night and we felt very safe. The property is well cared for and we would definitely go there again. We enjoyed the short ride to the downtown area. The bike riding trails were in close proximity. Garner and Marylu give it a thumbs up!

Apartment in Peterborough

A serene landscape showcases a view of Mt. Monadnock in the distance, surrounded by a lush tapestry of trees displaying varying shades of green. The foreground features an open grassy area bordered by a rustic fence, contributing to the sense of tranquility.

4.92 out of 5 average rating, 189 reviews

Private Apartment with a Mt. view

BradRating, 5 stars5 months ago

Cold Comfort Farm offers a wonderful setting and view for anyone who wants a true New Hampshire experience. It reminded me of my youth growing up nearby. Jo was completely welcoming.

A cozy living room is shown with a wall-mounted television and a rustic brick fireplace. Two comfortable recliners are positioned in front of the fireplace, with a stacked wood storage area visible beneath the mantel. Natural light filters through the window blinds.

5 out of 5 average rating, 10 reviews

Privacy, View, Amenities, Gym, Garage included too

AndreaRating, 5 stars1 month ago

Laura’s place was better than expected. The pictures don’t do it justice. I wish I knew about it 4 years ago when my son started college. I would’ve stayed there every year. They are very welcoming. The suite is amazing and the scenery is beautiful. I wish we could’ve stayed there longer.

The Victorian Inn is set on a gently sloping green lawn, framed by vibrant fall foliage. The three-story structure features a wide front porch with white railings, large windows, and a well-maintained exterior, contributing to its historical charm.