
Waterfront holiday rentals in Chesterfield
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Top-rated waterfront rentals in Chesterfield
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"Beau Overlook" Enjoy 2 states from 1 great spot!
Come enjoy LOGISTICS to the Green Mountains of VT & the heart of the DACKS in one sweet spot. "Beau Overlook Cottage" perched high on the banks of the BOQUET RIVER, with sweet sounds of water tumbling over river rocks below. This home is situated 2 miles north of the Lake Champlain ~ Boquet River Delta. The beautiful LAKE scene at the sandbar of the delta must be seen to be appreciated. This relaxing sanctuary will provide an upscale and sophisticated home, whose logistics cannot be beat!

Gateway to the Adirondacks on the River “The West”
Situated directly on the Au Sable River, where the West and the East branch meet, you'll find this comfortable duplex, located in Au Sable Forks, the "Gateway to the Adirondacks". The West offers a fully equipped kitchen, three bedrooms, full bath, and comfortably furnished living room and Wi-Fi. Conveniently located within walking distance to grocery stores, pub, eateries, and entertainment. Enjoy fishing, biking, hiking, Whiteface mountain and Lake Placid. Come stay and enjoy the Adirondacks

Secluded Village Gem: Cozy Studio Overlooks River!
Unwind in a charming studio retreat ideally located in Shelburne Village. Peace and privacy on the edge of the nature preserve overlooking the LaPlatte River. Perfect for travelers visiting the Burlington area. 9 miles to downtown BTV. Gorgeous space with lovely furnishings. Super comfortable bed and leather seating. Private entrance. Compact kitchenette. Dedicated workspace and high-speed internet. Dog friendly. A/C for the occasional hot summer day. Miles of trails steps from your front door!

Private Lakefront Suite - Best Views on The Lake!
Welcome to VT’s most beautiful lakefront property! Relax in one of many Adirondack chairs while enjoying incredible sunsets over Lake Champlain and the ADK Mtns. The 1 BR suite shares no space with the main home and has its own entrance and bathroom. Just imagine having one of VT’s premier lakefront wedding venues all to yourself. Just bring the s’mores to toast at our lakeside fire pit. You certainly will not be disappointed! Please read the full description about the rental prior to booking.

The Brookside Cabin
Our Cabin is nestled in the woods of the Adirondack Mountains. The Cabin is behind our family home. We are on a country road close to two towns. Our area offers many amenities such as fishing, hiking, boating, golf, hunting , wine tasting, leaf peeping. The cabin is heated by a wood stove and is the only heat source. “Wood Stove will injure a small child. Fast moving water in brook. Children 7 and up is ok with pre approval. The outside shower is heated, hot water available mid April -Nov.

Quiet 3 Bedroom Cottage on Lake Champlain
You'll have a relaxing visit at this cozy, comfortable family camp. Enjoy swimming, kayaking and hiking. Explore gorgeous Lake Champlain or enjoy the view from the porch. The sunrises are spectacular! Lake Champlain is known for great year-round fishing. Tip: Bring your water shoes for maximum swimming comfort. Hop on the Essex Ferry to Vermont to experience shopping, art, restaurants and museums. The Shelburne Museum and ECHO, Leahy Center for Lake Champlain are perfect for families.

The cutest little cabin in the Adirondacks!
NO ADDITIONAL FEES! Wake up to the sounds and sights of a relaxing Adirondack stream, next to the Barton Brook in charming, little Elizabethtown, NY. The building is in our backyard and the inside is roughly 7x7 with one single twin sized bed, dresser with three drawers, a dorm sized fridge, coffee maker, outlets, a light inside and on the open porch. We have a screened hammock next to the cabin. Enjoy your morning coffee or read a book sitting in the Amish rocker by the outdoor fireplace.

Wilmington Range Log Cabin on the AuSable River
Adirondack log home located on the Ausable River with mountain views of Whiteface Mt and the Wilmington Range. Enjoy the Adirondacks based out of this cute log cabin with rustic charm, views, and peacefulness, located a minute away from Wilmington town center and 5 minutes away from Whiteface Mt Olympic ski area! This 2.5 bedroom charming log chalet-style home is the perfect size for a week or weekend getaway to the Adirondack Mountains. A staircase leads from the home to a riverside deck.

Bright new cottage in exquisite Vermont setting
Relax in "Findaway" cottage. Centrally located between Burlington and Montpelier and directly adjacent to Sleepy Hollow cross country ski and bike area, Birds of Vermont museum and the Vermont Audubon Center. Settle in and relax, hike right out the door, or sip a drink on the deck overlooking a beaver pond where you may see beaver, otters, deer, birds or even a moose! Surrounded by gardens and not far from downhill skiing and hiking options, swimming, sailing, dining and Lake Champlain.

The Barn in Shelburne
Completely renovated in 2024! Located at the end of a quarter mile driveway on a 60 acre oasis in the heart of Shelburne, The Barn is a ready for your next visit. The Barn has a private trail network, a swimming pond, views of the Adirondacks & Green Mtns and is 100% powered by solar energy. The Barn has a completely renovated kitchen, two bedrooms, two bathrooms, brand new queen & king mattresses, and a pull out couch (perfect for kids) We live next door & look forward to hosting you!

New, quaint 1 bedroom in downtown Plattsburgh
1 bedroom with 10ft ceilings with lots of natural light. Walking distance to amazing restaurants, craft breweries, walking and biking trails, museums, theater, parks, boating, and skiing. Close to SUNY and CCC campuses and UVM/CVPH hospital. Airport is 5 minutes away. Lake Champlain and boat basin are only a 5 minute walk. Lake Placid, Burlington and Montreal are an hour or less away. Plenty of parking for vehicles and anglers with their boats. Lots of local history to explore.

The Covered Bridge Cottage- Ausable Riverfront
Situated directly by the Ausable River and surrounded by beautiful vineyards and gardens you will be immersed in nature at any time if the year. It's sure to restore the soul. The gentle rumble of the river is ever present as you look out over the natural beauty. During the summer cool off in the river and come back to the screened in porch for an evening meal. In the winter fire up the pellet stove and get cozy. 15 minutes to Whiteface and Keene and 25 Minutes to Lake Placid.
Popular amenities for waterfront rentals in Chesterfield
Waterfront apartment rentals

The Best Nest- Beautiful Lake Champlain access

Dog Team Falls Apartment - Minutes from Middlebury

Four Pines on Lake Champlain

The Bootlegger Outlaw Hideout @The Pony Farm Ranch

New Modern Studio- Hop Skip & Jump to Waterfront

Night Sky Niche: ADK High Peaks

East Wing 2nd Floor Apartment

Mary's House in Moretown Village
Waterfront house rentals

Spacious Lakefront Retreat w/Stunning Views

Brand new Beautiful Modern Clean Home On River

Lake Dunmore Getaway — Foliage Views & Ski Retreat

Summer View Lake House

Breathtaking Views Near Lake Placid and Whiteface

Sauna, Dock & 180° Views – Lakefront Retreat

Waterfront, Hot tub, Pet friendly, 5min-White face

The Brook House Downstairs
Waterfront apartment rentals

Wolf Jaw Lodge u61 - Lake Views!

One level condo in the heart of Stowe Village!

5 Mins from Whiteface Mountain Ski Resort

Lakeside #1 STR # 200347

Adirondack Studio Retreat–Cozy Lake Placid Escape!

Modern Farmhouse Condo: fast WiFi+close to it ALL!

1br Deluxe Unit -Nature Escape-Smugglers' Notch ML

*Seasonal Rental* Beautiful Condo 3 NearSugarbush
Quick stats about waterfront rentals in Chesterfield

Total holiday rentals
Explore 20 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $104 SGD per night before taxes and fees

Verified guest reviews
Over 1,100 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Chesterfield holiday rentals include wifi 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!
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- Sugarbush Resort
- Parc Safari
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Autumn Mountain Winery
- Country Club of Vermont
- Ethan Allen Homestead Museum
- Burlington Country Club
- Leahy Center for Lake Champlain
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- Titus Mountain Family Ski Center
- North Branch Vineyards
- Cozy Cottages & Otter Valley Winery




