Kid-friendly vacation rentals in Cheshire County

4.98 out of 5 average rating, 103 reviews

An outdoor tub is situated on a wooden deck, surrounded by vibrant autumn foliage. A red faucet provides a natural flow of water, while a small bowl of floating objects rests nearby. In the background, a glimpse of a serene lake can be seen through the trees.

Cabin in Stoddard

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.

4.97 out of 5 average rating, 232 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.

A rustic building with wooden siding is partially surrounded by a foggy landscape. An elevated deck with rocking chairs invites relaxation. The entrance features glass doors flanked by large windows, allowing natural light to illuminate the interior. Surrounding greenery creates a serene atmosphere.

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.

4.99 out of 5 average rating, 175 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.

4.82 out of 5 average rating, 271 reviews

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

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, 161 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.

4.93 out of 5 average rating, 211 reviews

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

Home in Keene

The Brick House on Washington Street

Three guest bedrooms in a Colonial home on Washington Street make a great launchpad for visitors to Keene. From here, it's a pleasant walk or drive to Downtown restaurants, the theatre and shops. The Sterling family has owned this pretty place since 1982 and a design studio operates in the barn portion of the space. The open living room with TV and original fireplace adjoin a "tea room" with a bright bay window. Family chef-approved, guests are welcome to use the spacious kitchen.

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!

4.96 out of 5 average rating, 290 reviews

The image captures a serene riverside view, featuring lush greenery along the water's edge. The gentle flow of the river is visible, creating a tranquil atmosphere. A hint of architectural elements, such as a decorative roofline and surrounding foliage, provides a connection between the natural and built environments.

Loft in Peterborough

1850 Waterfall Mill-Loft Style Chic

IMMACULATE COUNTRY HOME W/ FAST WiFi in fresh air New Hampshire. Snuggled in on a quiet street, yet steps away from DOWNTOWN, two "Mini Whole Food" markets! State-of-the-art gourmet kitchen fleshed out with organic spices, wares for entertaining, and other luxuries such as a rReverse Osmosis drinking faucet. Stunning sunlit water views and soothing water sounds! Beautiful antique furnishings and marble finishes add to the unique beauty of this New England home.

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, 263 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, 187 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.

Vacation rentals for every style

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Popular amenities for Cheshire County kid-friendly rentals

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Free parking on premises

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Kid-friendly house rentals

4.94 out of 5 average rating, 123 reviews

A spacious deck extends from the house, equipped with an umbrella and several chairs, providing a view of the encompassing greenery and mountains. The home's exterior features warm brown siding and solar panels on the roof, set against a bright blue sky.

Home in Brattleboro

Spacious Brattleboro home on river, walk to town

ThomasRating, 5 stars1 month ago

It was perfect for my overflow guests attending a weekend family reunion!

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.

4.99 out of 5 average rating, 218 reviews

Lovely Brick Schoolhouse

GretchenRating, 5 stars1 week 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 stars1 week 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!!!

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.

4.89 out of 5 average rating, 103 reviews

Peaceful Beautiful Mountain Home Spectacular Views

LibbyRating, 5 stars3 months ago

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

5 out of 5 average rating, 154 reviews

Home in Keene

Downtown Hot Tub Escape

KylaRating, 5 stars1 week 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!

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!

5 out of 5 average rating, 103 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 stars1 week 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.

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.

4.95 out of 5 average rating, 341 reviews

Cozy Train Depot in Putney Vermont

JudithRating, 5 stars2 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

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

MariaRating, 5 stars2 weeks ago

My husband, our pups and I had a great stay at this loft. The space was clean and easy to get in. Parking was not a problem at all. There is a church that rings its bells on the hour, but they didnt bother us at night at all. The shower was a bit cramped, but worked for us. If youre on the bigger side or taller, it might be a bit tight. Overall, great place and Naomi was attentive and provided clear instructions for everything. We will definitely stay here again when we get a chance to return.

A comfortable living space is featured, showcasing a brown sofa and two stylish leather chairs. A wooden side table complements each chair. A wall-mounted TV is positioned across from the seating area, with a desk and chair available for work purposes. Natural light filters in through the window.

4.96 out of 5 average rating, 25 reviews

"The Ramsdell Suite @ The Large House"

BarbaraRating, 5 stars1 month ago

Another enjoyable & super excellent stay at Shane's place! Very comfortable & safe, impeccably clean first floor apartment. Shane is an extremely kind, attentive, super excellent Host!

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, 4 reviews

Dover by Downtown

PatriciaRating, 5 stars3 months ago

We enjoyed our stay and can recommend Dover by Downtown for an uncomplicated stay in Keene. The second floor apartment is located within walking distance from a grocery store as well as many restaurants, while the surrounding neighborhood is quiet and pleasant. It was exactly what my mother, my daughter, and I needed after a long day of touring by car. Julie promptly replied to all of our questions, and the driveway parking is conveniently located near the front door. Thank you Julie, for being a great host during our stay in New Hampshire!

Apartment in Town of Rockingham

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, 185 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.

Apartment in Town of Rockingham

A spacious studio is depicted, featuring a cozy seating area with a blue couch and a patterned loveseat. A large wooden dining table is positioned nearby. The room is accented by vibrant artwork and is illuminated by natural light from two windows, complementing the warm wood flooring.

4.95 out of 5 average rating, 274 reviews

Stunning Studio in historic Downtown Bellows Falls

BradleyRating, 5 stars3 weeks ago

This is one of the favorite places I've stayed at. The unit had character and the building did as well. Great high ceilings, spacious and well decorated. The village is lovely and walkable. Remy was pleasant and is involved with one of the restaurants downstairs, which is a must for a meal while you are in town. Can't speak highly enough of the experience.

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, 9 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.