
Waterfront holiday rentals in Chesterfield
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Top-rated waterfront accommodation in Chesterfield
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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!

Mountain side acres
10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

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 Round House on the Connecticut River
"River Round" offers guests the finest waterfront on the New Hampshire side of the Connecticut River with a private dock, panoramic views, and spectacular sunsets. A four-season destination close to skiing at Okemo, Stratton, Sunapee and more. Circular main floor with cathedral ceilings, exposed beams, and a fully-equipped chefs kitchen along with three bedrooms and three baths. Walk-out basement holds a large bar and kitchenette, two additional bedrooms and full bath. Enjoy life on the River!

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 .

Private Brook Chalet: Hot Tub, Fire pit, Mt. Snow
The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food VT has to offer.

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.

Beautiful Log Cabin on Highland Lake
Take it easy at this unique and tranquil getaway. A gorgeous log cabin nestled right on Highland Lake in Washington, NH. An outdoor lovers paradise that welcomes you any season. Nearby Mount Sunapee, Mount Manodnock, Crotched Mountain, Pillsbury State Park and Pats Peak. fall foliage, fire pit, grilling, ATV trails ice fishing, nearby skiing, snowmobile trails boating, kayaking, swimming, fishing Get the full New England experience at this incredible lakeside location!

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.
Popular amenities for Chesterfield waterfront rentals
Waterfront apartment accommodation

Cozy Brookside Getaway

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Connecticut River Odyssey

Suite 23 - Spacious Sunny 2-BR with Mountain view

Globetrotter Retreat too - Minutes to the Mountain

River View Apt in Shelburne Falls Historic Village

On the Water at North Bridge Cove, Patio and Sauna

Riverside Retreat – Cozy 2-Story Getaway!
Waterfront house rentals

Lake Escape

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

Our Pondside Cabin

Modern 3-bedroom A-frame in Londonderry w/ Pond

The Grafton Chateau

Cozy Riverfront Home in beautiful Jamaica

Lakefront, view of ski mtn, fireplace, sauna

Newer Home on quiet 200 acre lake - sleeps 6
Waterfront condo accommodation

Updated light filled condo @ Mt Snow/ HayStack ski

2BR Riverfront 2nd-Floor | Balcony |

Flowers & Falls Spot House

River House: walk to campus, town, Clark & more

Private condo w/stunning view of lake frontage
Quick stats about waterfront rentals in Chesterfield

Total holiday rentals
Explore 10 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $126 AUD per night before taxes and fees

Verified guest reviews
Over 260 verified reviews to help you choose

Wi-Fi availability
10 of Chesterfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
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- Family-friendly rentals Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a patio Chesterfield
- Rentals with a fire pit Chesterfield
- Rentals with lake access Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Waterfront rentals Cheshire County
- Waterfront rentals New Hampshire
- Waterfront rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Pats Peak Ski Area
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Mount Snow Ski Resort
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Mount Sunapee Resort
- Mount Greylock
- Southern Vermont Arts Center
- Smith College
- Mount Holyoke College
- Emerald Lake State Park
- Mount Monadnock
- Massachusetts Museum of Contemporary Art
- University of Massachusetts Amherst
- Look Memorial Park
- Magic Wings Butterfly Conservatory and Gardens




