
Vacation rentals with lake access in Chesterfield
Find and book unique lake access rentals on Airbnb
Top-rated lake access rentals in Chesterfield
Guests agree: these lake access rentals are highly rated for location, cleanliness, and more.

Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

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.

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!

Spacious Loft with View
Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

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

Lakefront, view of ski mtn, fireplace, sauna
Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

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.

Cozy waterfront cabin Perkins Pond
Come relax, unwind and enjoy the year round beauty and fun at our cabin on Perkins Pond! Many activities to enjoy with each season.. Kayak, canoe, fish and swim or float, nap on the hammock in summer months.. Walk, hike and enjoy the awe of Fall color.. Snowshoe, skate, ice fish, cross country ski on the frozen pond during winter and enjoy downhill at Mt Sunapee just 8 min away or just relax by the wood stove!! Make special memories with your family and friends here at our special place!!

Cozy Vermont Antique Sugar House with Fireplace
Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Highland Haus AFrame Lake Access Vintage 70s Charm
Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!
Popular amenities for Chesterfield lake access rentals
Lake access house rentals

The Boat House on Granite Lake

Wachusett Mountain Get-Away

Willow Falls Home ~Hot tub & Waterfront

@SunapeeSeasons—Across from Dewey Beach, Lake View

Luxury King Suite, fireplace, bunkbed- Farmhouse 4

Family Friendly Lakefront Home

Large Home in Peaceful Historical Village

The Grafton Chateau
Lake access apartment rentals

Luxury 2 Bedroom 202B

Beautiful 2 Bedrooms in Mountains w/ full kitchen

Lakefront Orange Vacation Rental - Pet Friendly!

Connecticut River Odyssey

Westminster Lodge at Ryan's Ranch

Sunny Apartment with Goats

Luxury Condo*3BD3BA*Walk/Shuttle to lift

Paradise on the pond
Lake access cottage rentals

Willow Tree Cottage on Peaceful Mountain Lake

Tiny Cottage on Spofford Lake

"Trails End" Lakeside Cottage in Small Town USA

Waterfront Retreat on Chalk Pond

Cozy Cottage in the Berkshires

Country Cottage

Lake Wyola House Shutesbury Massachusetts

Love the outdoors? This is the place for you!
Quick stats about vacation rentals with lake access in Chesterfield

Total vacation rentals
Explore 20 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at ﺩ.ﺇ441 per night before taxes and fees

Verified guest reviews
Over 220 verified reviews to help you choose

Wi-Fi availability
20 of Chesterfield vacation rentals include wi-fi access

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

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




