Waterfront holiday rentals in Chesterfield

Globetrotter Retreat - Minutes to the Mountain

Newly renovated, fully furnished apt in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt sleeps 4 people in comfort. Private balcony overlooks rolling river. Steps from many restaurants, bars & shopping. Supermarket is a short walk. FreeMoover bus stop across the street - leave your car parked & ride for free to local destinations! No guest under 18 years old.

Peaceful Mill with Waterfall - Top 1% 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 remote workspace

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Chalet Sonsie: A Sweetwater Stay

Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace (our apologize but it is currently not working) with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

Sugar River Treehouse

Welcome to Sugar River Treehouse! If you’re looking for serenity, peace and quiet, in the most unique, breathtaking, beautiful setting, you have found it. On top of the trees, overlooking the Sugar River in the quaint town of Newport, NH you will find plenty of year round activities including swimming, floating, fishing on the beautiful, clear Sugar River, right outside the back door. You will find the treehouse sits up in between 2 beautiful northern hemlocks and is fully equipped inside.

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Swiss Chalet Family Retreat!

Welcome to our family's Swiss style chalet! Inspired by trips to Davos, Switzerland, my grandparents built the chalet in the 1950s to be a family playhouse and gathering spot for their 6 children. It's kind of magical. Today, our large extended family still enjoys holiday celebrations here every year. Our kids love exploring the woodland trails and swimming in Center Pond. We hope you love it as much as we do! Note: the building also has two apartments on the first floor.

Silk Purse Cottage on Baker Brook

The "Silk Purse" started life in the 60's as a 10x40 mobile home. Easy vehicle access and fast wifi are great for remote work. 20 minutes to Brattleboro, 30 to Stratton, 25 to Mt. Snow, 40 to Magic Mt. ski areas! The screened porch is a relaxing place to have coffee or cocktails. Extra windows add interior light in this shaded woodland setting, and a beautiful 12x14 addition with a skylight and a full wall of glass give an unobstructed, private view of the stream.

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.

Frosted Willows

Your family will be close to everything at this sunny, centrally located home on the Whetstone Brook. Just 0.6 miles from downtown Brattleboro, you can walk to shops, cafés, galleries, and more. Nestled in a quiet neighborhood, the house offers a peaceful place to relax after a day of exploring. Listen to the brook from the backyard, enjoy local adventures, and settle into a space that feels like home—perfect for a weekend getaway or a longer Vermont stay.