
Waterfront holiday rentals in Chesterfield
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Top-rated waterfront rentals in Chesterfield
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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

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.

Cozy and Romantic Granite Lake Cottage Getaway
Welcome to "Corgi Cottage" ~ your private peaceful getaway to pristine Granite Lake. Enjoy sunrise over the lake from the deck and sunset over the backyard barn. In between, spend the day on the lake in your private sandy cove with dock, fishing, hiking or relaxing. Three mile lake road for walking or biking. The area offers many hiking trails and Mt. Monadnock only 30 minutes away. Small convenience store offers basic amenities while Keene’s many shops and restaurants are only 15 minutes away.

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

Cottage beside a waterfall
Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

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.

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.

Spacious Brattleboro home on river, walk to town
Spacious 3,000 sq. ft. home with 4 bedrooms (3 queens, 2 twins) and 4 bathrooms, 3 en-suite. Enjoy a formal living room with grand and upright pianos, a cozy TV room, and a fully equipped kitchen with eat-in area leading to a deck with stunning river and mountain views. Formal dining seats 12. Expansive grounds are perfect for relaxing or hosting special events. Just a 10-min walk to Brattleboro’s Main Street shops, cafes, and culture.

Log Cabin: Amazing Views, River Frontage, Hot Tub
A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.
Popular amenities for waterfront rentals in Chesterfield
Waterfront apartment rentals

Beautiful lake side getaway, quiet.

Cozy Brookside Getaway

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

Suite 23 - Spacious Sunny 2-BR with Mountain view

Globetrotter Retreat - 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

Wachusett Mountain Get-Away

1850's VT Farmhouse on the River

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

The River House

19th c. Barn in The Berkshires

Cozy Riverfront Home in beautiful Jamaica

Lakefront, view of ski mtn, fireplace, sauna

Newer Home on quiet 200 acre lake - sleeps 6
Waterfront apartment rentals

Updated Light filled condo @ Mt Snow /golf/ trails

2BR Riverfront 2nd-Floor | Balcony |

Flowers & Falls Spot House

Updated 2nd floor 2BR condo @ Mt Snow / HayStack

Private condo w/stunning view of lake frontage
Quick stats about waterfront rentals in Chesterfield
Total rentals
10 properties
Nightly prices starting at
$117 SGD before taxes and fees
Total number of reviews
320 reviews
Pet-friendly rentals
10 properties allow pets
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Destinations to explore
- Plainview Holiday rentals
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- Rentals with lake access Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a patio Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with a firepit Chesterfield
- Family-friendly rentals Chesterfield
- Waterfront rentals Cheshire County
- Waterfront rentals New Hampshire
- Waterfront rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Manchester Country Club - NH
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Mount Tom State Reservation
- Mount Snow Ski Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- The Shattuck Golf Club
- Hooper Golf Course
- Crotched Mountain Ski and Ride
- Brattleboro Ski Hill
- Ekwanok Country Club
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Mount Sunapee Resort
- Baker Hill Golf Club