We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Chesterfield

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Loft in Keeseville

Adirondack Gem in the Champlain Valley/VT Views

Our country home is nestled in a peaceful wooded area overlooking Lake Champlain and the VT Green Mtns . The 900 sq ft Loft is private and welcoming, with many thoughtful details for your comfort and total relaxation. Cuddle up with comfy chairs, cozy throws and an abundance of books and magazines. It is so quiet, and the beds so comfortable, that a restful night's sleep is almost a guarantee. Kayaking, canoeing, and fishing opportunities abound with water access close-by. Very kid-friendly.

Chalet in Jay

Adirondack Base Camp Cabin

Cozy Mountain Chalet in Jay, NY on beautiful Glen Road. Only .7 miles to the Jay Covered Bridge, 3 miles to the Jay Mountain summit trail head, 7 miles to Whiteface Mountain, and 16 miles to Lake Placid. Keene and Keene Valley trail heads are only minutes away. The cabin has 3 acres of wooded property with a front driveway as well as a back access drivweway which is nice to walk. There is Satellite TV and wifi. There is good cell coverage. World Class Fishing, Ausable Rivers are close

Rental unit in Clintonville

Cozy Rustic Apartment

We are located on the famous Ausable River within a 30 minute drive to many of the High Peak trails, the beautiful Ausable Cham, and Whiteface mountain. We are 5 miles from Interstate 87. The apartment can be a cozy retreat after spending a day exploring in the Adirondacks. Spend time strolling down to the river to enjoy the scenic views or enjoy quality family time. The apartment had a unique style of it's own that will provide you a comfortable and reasonable price place to stay.

Home in Wilmington

THE VIEW! THE VIEW! THE VIEW!

A 1900 farmhouse that has been in the family for generations. Recently renovated to accommodate up to 5 guests, it is clean with simple furnishings and a SPECTACULAR VIEW! Located RIGHT ON NYS RTE 86 (close to the road) with easy access to nearby attractions. The house is split in 2 and is designed for 2 families. I rent out "The View" using airbnb exclusively. My wife and I reside in the back portion of the house with a separate entrance and separate parking.

Home in Port Kent

18 Lake, overlooking beautiful Lake Champlain

Welcome to 18 Lake. Situated in beautiful, quiet, Port Kent, NY., this is the perfect place to relax and to get away. People come from all across the country to tour the area on bicycles in summer, and from all over the world during the winter for Lake Placid's winter sports. In fall, the colors are incredible. You will find golf about 1/2 mile away, and other attractions such as Ausable Chasm, High Falls Gorge, orchards, boating, hiking, and more close by!

Cabin in Lewis

Adirondack Cabin Sanctuary

This charming cabin hides in thirteen private wooded acres. Gorgeous views include a babbling brook, small pond, and delightful woodland paths. The cabin boasts hardwood floors, a stunning fireplace, functional kitchen and bathroom spaces, safe drinking water, electricity, an outside deck and a screened porch with firepit. Short drives will bring you to Whiteface Mountain, Lake Placid, and Lake Champlain.

Tiny home in Jay

Cozy tiny house with endless Adirondack adventures

Center of: trout fishing in the AuSable river, hunting,skiing and hiking. 20 minutes from Whiteface Mt. ski center ,1/2 hour from Lake Placid and all Olympic venues, 20 minutes from High Falls Gorge. 5 minutes from grocery, gas,and deli. Enjoy an outdoor firepit ,barbecue and picnic area while relaxing in a country side setting with beautiful views of the AuSable River and Adirondack hillsides.

Cabin in Schuyler Falls

Hikers Base Camp Cabin

Newly renovated building on 52 private acres with nice walking trails. Overlooks small trout stream and active beaver pond. Located at the Northeastern entrance to the Adirondack Park, we are conveniently placed to begin an ADK adventure. We are familiar with most of the trailheads and are on site to help in any way we can. We do not allow campfires on the property because of the high fire risk.

Home in Keeseville

The Paddle Inn

Our house is very open and spacious. It is designed to get around easily. There are multiple places to sit and eat or enjoy nature. The house has numerous windows and is well lit. There is a lot of deck space and a big back yard for games. We are always friendly and open, just down the road if anything is needed! We love meeting new people and do what we can to make your stay comfortable!

Guesthouse in South Hero

Rustic 5th wheel camper close to lake.

You'll always remember your time at this unique place to stay. Camper living in Vermont winters. Owners on-site. Camper is winter ready and offers an affordable place to stay close to the lake views. Plenty of on-site parking for boats/trailer. We are close to the NY ferry but you don’t need to take a ferry to get to our place.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Chesterfield vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Chesterfield

Guest suite in Elizabethtown

Bell Crest Suite

Guest suite in Hinesburg

Boston Magazine Pick! Barn Loft

Rental unit in Wilmington

LITTLE TIMBERDOODLE

Guesthouse in Keeseville

Colvin's Cabin in the Adirondacks

Cabin in Keeseville

Lovely Cabin on Farm with Sauna, Porch, Mtn Views

Rental unit in Port Kent

Beautiful Lake and Mountain Views!

Tiny home in Au Sable Forks

Modern Tiny House

Place to stay in Peru

The Brookside Cabin

Quick stats about vacation rentals in Chesterfield

Total rentals
80 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
3.6K reviews
Nightly prices starting at
$70 before taxes and fees

Frequently Asked Questions

What are the most popular amenities for Cottage Rentals in Chesterfield?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Chesterfield?
Experience the best of Chesterfield with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Chesterfield have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Chesterfield?
Four-legged friends are welcome in Chesterfield. Choose from more than 40 vacation rentals for guests traveling with pets.
Do cabin rentals in Chesterfield have free parking?
Absolutely! We offer over 10 cabin rentals with free parking in Chesterfield. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Chesterfield?
Yes! Work meets play with ease at over 30 vacation rentals in Chesterfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Chesterfield?
Chesterfield has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Chesterfield have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Chesterfield. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore