
Waterfront vacation rentals in Chesterfield
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Chesterfield
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Peaceful Mill with Waterfall - 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 remote workspace

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.

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!

Cozy Comfort on 250 Acre Private Estate
If you’re looking for serenity, peace and quiet, you've found it, amidst a 250 acre private estate. On a lake at the end of a mile long driveway (well plowed in the winter) Is Snowshoe Cabin. Built in 1929 as the garage for "Lakefalls Lodge, it's been completed renovated into a luxurious, cozy home with modern amenities. Guests rave about "views of the snowy pond while you’re warm inside" from heated floors and a wood burning stove with free firewood. Spikes provided for wonderful winter walks.

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

~Luxury Tiny Cabin~
Enjoy an intimate weekend escape in our 400 sq ft Tiny Cabin, located in Southern Vermont! This Home overlooks gorgeous hardwoods and seasonal foliage. Listen to the sound of the brook bustling by while nestled on the spacious front porch, sipping a hot cup of coffee or cocoa! 'Tis the season for glamping and our luxury tiny home experience is just what the doctor ordered! Make sure to cross this off your bucket list; about 45 minutes from Mts Okemo and Killington, 5 minutes from local stores!

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.

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 .

Willow Falls Home ~Hot tub & Waterfront
Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

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.

Classic Vermont A-Frame | Fire Pit | Near Stratton
Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.
Popular amenities for Chesterfield waterfront rentals
Waterfront apartment rentals

Cozy Brookside Getaway

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

49 River Street

Dog heavenly! Private, beautiful and relaxing.

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
Waterfront house rentals

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

The Crowcroft House

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

Lakefront, view of ski mtn, firepit, kayaks, dock

The Grafton Chateau

19th c. Barn in The Berkshires

Cozy Riverfront Home in beautiful Jamaica

Historic Mill • Near Okemo • Fireplaces • Wi-Fi
Other waterfront vacation rentals

Picturesque Cabin on the Mettowee

Stratton Summer House | Trails + Swim Holes + AC

The River House

Cozy Cottage Loft and Retreat

Cozy Riverfront Cabin-Ski, Swim, Fish, Float, Hike

Riverside Farmhouse

The Boathouse - A rustic and cozy lakeside cottage

Divol Pond Cabin
Quick stats about waterfront rentals in Chesterfield

Total vacation rentals
Explore 10 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at G$18,828 GYD per night before taxes and fees

Verified guest reviews
Over 260 verified reviews to help you choose

Wi-Fi availability
10 of Chesterfield vacation 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
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- Rentals with a washer and dryer Chesterfield
- Rentals with outdoor seating Chesterfield
- Rentals with a patio Chesterfield
- Pet-friendly rentals Chesterfield
- Family-friendly rentals Chesterfield
- Rentals with a fire pit Chesterfield
- Rentals with lake access Chesterfield
- Waterfront rentals Cheshire County
- Waterfront rentals New Hampshire
- Waterfront rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Stratton Mountain Resort
- Jiminy Peak Mountain Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Mount Sunapee Resort
- Emerald Lake State Park
- Smith College
- University of Massachusetts Amherst
- Mount Monadnock
- Crotched Mountain Ski and Ride
- Mount Holyoke College
- Southern Vermont Arts Center
- The Montague Bookmill
- Mount Greylock
- Camp Plymouth State Park
- Jamaica State Park





