Family-friendly vacation rentals in Chesterfield

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Top-rated family-friendly rentals in Chesterfield

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy living area features two black leather armchairs with white throws, positioned near a brick fireplace. A stylish rug covers the floor beneath, while natural light filters in through the large windows, illuminating the space with a welcoming ambiance.

Home in Lake Placid

4.99 out of 5 average rating, 137 reviews

My Blue Heaven—Family Home in the Heart of Lake Placid

Watch the world go by from one of the rockers on the wraparound porch. Spacious, inviting vintage home with updated decor. Two eating areas, cozy nook with wood stove. Walk to town & lake. Lots of space to relax & unwind. Equipped with desks & Wi-Fi for remote work. We look forward to hosting you and hope enjoy the magic of Lake Placid! We welcome parties of 10 or less with a maximum of 6 adults. No parties/events. No smoking. (Town Permit # STR-200292) Guests have access to the entire home with the exception of the garage interior, the basement and an owner's closet. We're available anytime via cell phone and have a property manager nearby who is available to address any issues. Set in a quiet neighborhood in the center of town, stroll from here to boutiques, cafes, and restaurants. Lake Placid, Mirror Lake and the original Olympics facilities are all within walking distance. Hop on the shuttle to reach Whiteface. Walk or drive as you like. A shuttle to Whiteface is available around the corner as well. We provide starter toilet paper, hand soap, shampoo, 2 hair dryers, all bed linens including pillows, towels and basic cleaning supplies. The kitchen is meant for cooking with pots, pans, mixing bowls and more! There is a supermarket right up the road (and plenty of speciality markets around town.) Happy eating!

Top guest favorite

The exterior of the chalet features a warm and inviting facade with a covered entryway, accented by a star motif. Surrounded by trees, the driveway is lined with gravel, leading to a spacious front yard with decorative seating and a sauna barrel.

Home in Wilmington

4.94 out of 5 average rating, 220 reviews

Luxurious Chalet in the Woods!

CASCADE MOUNTAIN CHALET: Hot Tub, Sauna, 1 mile to Whiteface, 15 minutes to Lake Placid, Dog Friendly Fantastic 3 Bedroom (King beds), 2 Full Bath Chalet that sleeps 8 (queen-size foam mattress available to sleep up to 2 children). This home has a warm, stylish vibe in an ideal location! Amenities Include: Hot Tub, Fireplace, Finlandian Dry Sauna, Fire Pit, BBQ Grill, Deck, Huge Yard, Dogs welcome (no cats), fully equipped kitchen with 6 burner gas stove, granite counters, washer/dryer.

Top guest favorite

Home in Lake Placid

4.98 out of 5 average rating, 321 reviews

Bear Cub Lodge- An Adirondack Mountain Retreat

Spacious 3 Bedroom, 2 Full bathroom Adirondack retreat by the Olympic Ski Jumps and just 1.2 miles to the heart of town. Warm cozy fireplace and dining room/living room combo for family/friend gatherings. Many trails within walking distance for great hiking, X-County Skiing, and go from the back door to trails that lead to the Ski Jumps. Lots of room to spread out! Happy to help plan your vacation and share inside scoop on all things Lake Placid & Whiteface. Whiteface just 9 miles away.

Guest favorite

A cozy living area features a comfortable grey sectional sofa with colorful throw pillows, accompanied by a yellow armchair and a green ottoman. Natural light filters through a window, illuminating a light-colored coffee table positioned centrally on a carpeted floor.

Guesthouse in Saranac Lake

4.92 out of 5 average rating, 372 reviews

Village Cottage-Walk to Downtown

Very cute cottage is within walking distance to restaurants and dining, family-friendly activities, and nightlife. Good side yard with outdoor furniture. Enclosed porch for rainy days. Huge soaking tub. Our place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). We do not charge a pet fee but will charge for any damages incurred. This is a cottage next to where we live. We are self check in but you may run into us.

Top guest favorite

A wooden dock extends over calm waters, reflecting a clear blue sky dotted with fluffy white clouds. The distant mountains along the shoreline provide a picturesque backdrop, enhancing the serene lakeside environment.

Home in Addison

4.96 out of 5 average rating, 225 reviews

Brthtkng New Premier Lake Champlain Wfrnt Escape!

7/19/20 : UPDATE - We are fully compliant with all local, state and federal safety protocols. Call /text Us fir any questions, at 978-502-6282 . Be Well, Be Safe & We Look Forward to Having You as Our Guests! We are the #1 Premier Lake Champlain Breathtaking New Property with 250'+ Prime Lake Champlain West/Sunset/Adirondack Mtn. facing w/Amazing Sunsets & Jacuzzi Tub in Master Bath Overlooking Lake,Mountains & Amazing Sunsets and 250+ 5 Star Reviews!

Top guest favorite

A spacious kitchen features warm wood paneling and granite countertops. A large island with natural stone accents is surrounded by wooden stools. Stainless steel appliances, including a refrigerator and oven, are visible, along with ample cabinetry and windows providing natural light.

Cabin in North Creek

4.98 out of 5 average rating, 177 reviews

Gore Mountain Log Cabin Getaway

8 minutes to Gore Mountain. Perfect getaway for couples, family vacay, small sporting group, or long time friends. Log cabin located 5 mins to food & shopping. Summer offers gondola rides & short drive to lakes, fishing, boating; beautiful porch for morning coffee & lovely views. Gore Mountain in winter for skiing & snowboarding. 24 hour buffer between bookings from when guests check out. 3 night minimum stay on holidays. A/C unit in main room.

Guest favorite

Townhouse in Stowe

4.89 out of 5 average rating, 167 reviews

Stowe, Topnotch Resort-Best Mt & Luxury in Vermont

This beautiful Resort Condo is located in the award-winning, Top Notch Resort & Spa. Our spacious 2-bedroom, 2-bathroom condo is only 1 mile away from Stowe Mt. Resort while offering privacy and room to spread out on the resort’s 120 acres. It is perfect for families or couples. We are proud of our stellar reviews and competitive pricing. Newly updated, our home is ready for your perfect vacation! Enhanced Cleaning protocols in place!

Superhost

The exterior of a large, multi-level home showcases a wraparound porch with a red awning and is surrounded by well-maintained green lawns and decorative rocks. Tall trees provide natural shade, creating a welcoming outdoor atmosphere.

Home in Stowe

4.83 out of 5 average rating, 161 reviews

Great For Large Groups with Hot Tub

This property is not suited to noisy groups - please don’t book for partying. Recently renovated to meet every vacation need, this unique property has everything you require for a great trip. The property is huge, ideally located right on Mountain Rd - minutes to slopes, spas, breweries, restaurants, hiking, biking and swimming holes. With 4 large comfortable bedrooms, fun basement, huge living space with fireplace and private hot tub.

Guest favorite

The exterior of the cottage is shown, featuring natural wood siding and a welcoming front porch. Two colorful chairs are placed on the patio, and a BBQ grill is available nearby. Lush greenery surrounds the space, creating a serene outdoor setting.

Cabin in Lake Placid

4.94 out of 5 average rating, 266 reviews

BEST LOCATION! Stay Parkside and Walk Everywhere!

Come stay with us at the newly updated "Park Place", right in the heart of Lake Placid. You are walking distance to EVERYWHERE! Located on Teddy Bear Park, enjoy exquisite views of Whiteface mountain from the balcony while sipping your morning coffee. Whether you're traveling with the kids or having a much needed adult getaway, "Park Place" offers the ideal accommodations for your family and friends... RENTAL PERMIT #STR-200235

Guest favorite

A welcoming porch features bright turquoise walls and wooden steps leading up to it. Two hanging planters adorn the porch, while a small bistro table with two patterned chairs invites relaxation. Potted plants with vibrant foliage are positioned on either side of the steps.

Apartment in Burlington

4.94 out of 5 average rating, 130 reviews

No tariffs here! Will refund all taxes!

Now accepting reservations until Sept 2025. Situated on Lake Champlain in the desirable, artsy, historical south end of Burlington. Cozy, newly renovated, 1 BR apartment with 1 comfy queen bed, fully equipped kitchen, and all the comforts of home. Located on the city bike path, less than a mile to downtown. EV charger available. Longer stays: WORK at Hula Lakeside! Traveling nurses also encouraged!

Guest favorite

A two-story wooden vacation home is shown in a snowy landscape, surrounded by tall trees. The drive is accessible with parked vehicles visible. A green balcony is present above the entrance, and a snow-covered yard allows for outdoor activities in the serene setting.

Home in Jay

4.85 out of 5 average rating, 240 reviews

Family friendly house, walk to covered bridge!

4 bed, 2.5 bath vacation home is in the hamlet of Jay, NY. Great for groups & families! Kid friendly. Everything is close! Fishing and swimming in the Au Sable,Olympic Village of Lake Placid, Au Sable Chasm, Santa's Workshop, Lake Champlain, hiking, biking, and all the peaceful serenity of nature!

Top guest favorite

A living room area is furnished with a blue fabric sofa and armchair, accompanied by a wooden coffee table. Two lamps are positioned on side tables, providing illumination. A mirror and two framed pictures of nature are mounted on the wall, enhancing the relaxed ambiance.

Apartment in Cambridge

4.94 out of 5 average rating, 103 reviews

Smugglers' Notch, VT

The condo is part of Smugglers Notch Resort. The condo is in an excellent location - a three minute walk to the Village Center and the Village Ski Lift. Hiking and outdoor adventure a short walk away. The unit is an updated 2 bedroom, 2 bath condo with full kitchen, dining and living room areas.