Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Guest favorite

Loft in Keeseville

5.0 out of 5 average rating, 178 reviews

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.

Jan 4 – 11

G$28,112 GYD per night

Guest favorite

Apartment in Au Sable Forks

4.87 out of 5 average rating, 213 reviews

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

Nov 9 – 16

G$28,667 GYD per night

Guest favorite

Chalet in Jay

4.94 out of 5 average rating, 145 reviews

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

Dec 6 – 13

G$30,234 GYD per night

Guest favorite

Apartment in Plattsburgh

4.95 out of 5 average rating, 128 reviews

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.

Jan 19 – 26

G$20,913 GYD per night

Guest favorite

Apartment in Clintonville

4.95 out of 5 average rating, 148 reviews

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.

Mar 20 – 27

G$17,766 GYD per night

Guest favorite

Home in Port Kent

4.93 out of 5 average rating, 288 reviews

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!

Nov 7 – 14

G$22,837 GYD per night

Guest favorite

Guesthouse in Plattsburgh

4.95 out of 5 average rating, 229 reviews

Studio Cottage/Lake Champlain

This is a stand alone studio cottage with a lovely screened porch. Our cottage is located on our 7 acre residential lot. This is not a rural property. We work hard on all our gardens, with a lovely pond . Perfect spot to enjoy the Autumn foliage as well to go off leaf peeping in the Adirondacks. You can take advantage of the Plattsburgh City Beach and two Local State park beaches within a few minutes drive, all beaches offer a sandy beach, and swimming.

Mar 6 – 13

G$28,049 GYD per night

Guest favorite

Cabin in Lewis

4.98 out of 5 average rating, 135 reviews

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.

Oct 21 – 28

G$31,158 GYD per night

Guest favorite

Tiny home in Jay

4.96 out of 5 average rating, 170 reviews

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.

Nov 21 – 28

G$22,502 GYD per night

Guest favorite

Home in Keeseville

4.84 out of 5 average rating, 123 reviews

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!

Mar 12 – 19

G$30,228 GYD per night

Guest favorite

Chalet in Jay

4.99 out of 5 average rating, 209 reviews

Coleman Cabin

Welcome to our small but well-appointed chalet in the Adirondacks. We are located close to Whiteface Mountain, Lake Placid, Ausable Chasm, fishing on the Ausable River and 90 miles from Montreal. The neighborhood is called Ausable Acres where each home is separated from its neighbors by trees thereby offering considerable privacy

Dec 29 – Jan 5

G$26,999 GYD per night

Guest favorite

Home in Jay

4.98 out of 5 average rating, 326 reviews

Yinzer House - Close to Whiteface and Lake Placid

Just a 15 minute drive to Whiteface Mountain, this 1 bedroom modern Adirondack home offers everything you need to enjoy the perfect vacation. *No smoking and no pets allowed on property. *No more than two adults total allowed. *No early check-ins or late check outs allowed.

Feb 16 – 23

G$28,063 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chesterfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chesterfield's top sights

Giuseppe's Pizza Shop7 locals recommend

Harmony Golf Club and Community11 locals recommend

Turtle Island Cafe17 locals recommend

Ausable Brewing Company32 locals recommend

Indian Bay Marina7 locals recommend

Ausable Chasm164 locals recommend

Other great vacation rentals in Chesterfield

Guest favorite

Apartment in Shelburne

4.9 out of 5 average rating, 287 reviews

Secluded Village Gem: Cozy Studio Overlooks River!

Jun 22 – 29

G$29,189 GYD per night

Guest favorite

Guesthouse in Monkton

4.98 out of 5 average rating, 105 reviews

Beautiful, 1 BR guesthouse

Nov 19 – 26

G$29,337 GYD per night

Guest favorite

Loft in Upper Jay

4.97 out of 5 average rating, 326 reviews

Sugar House Creamery Carriage Barn

May 29 – Jun 5

G$28,999 GYD per night

Guest favorite

Guest suite in Weybridge

4.99 out of 5 average rating, 234 reviews

Beautiful 1 Bedroom Suite with private entrance

Dec 10 – 17

G$22,235 GYD per night

Guest favorite

Guesthouse in Keeseville

5.0 out of 5 average rating, 52 reviews

Colvin's Cabin in the Adirondacks

Jun 5 – 12

G$14,897 GYD per night

Guest favorite

Cabin in Keeseville

4.95 out of 5 average rating, 61 reviews

Lovely Cabin on Farm with Sauna, Porch, Mtn Views

Jan 17 – 24

G$23,721 GYD per night

Guest favorite

Place to stay in Peru

4.84 out of 5 average rating, 87 reviews

The Brookside Cabin

May 30 – Jun 6

G$17,249 GYD per night

Guest favorite

Cabin in Au Sable Forks

4.97 out of 5 average rating, 74 reviews

Moon Ridge Cabin *Hottub*

Sep 4 – 11

G$26,403 GYD per night

Show all

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
G$14,606 GYD 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 free parking, over 10 homes with wifi, 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 cabin rentals in Chesterfield?
Experience the best of Chesterfield with our cabin rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chesterfield have wifi?
Absolutely! We offer over 20 house 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 cottage rentals in Chesterfield have free parking?
Absolutely! We offer over 10 cottage 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.

Vacation rentals in Chesterfield

Top-rated vacation rentals in Chesterfield

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Chesterfield vacation rentals

Stay near Chesterfield's top sights

Other great vacation rentals in Chesterfield

Apartment in Shelburne

Guesthouse in Monkton

Loft in Upper Jay

Guest suite in Weybridge

Guesthouse in Keeseville

Cabin in Keeseville

Place to stay in Peru

Cabin in Au Sable Forks

Quick stats about vacation rentals in Chesterfield

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What are the most popular amenities for Cottage Rentals in Chesterfield?

How much does it cost to stay in cabin rentals in Chesterfield?

Do house rentals in Chesterfield have wifi?

Are there pet-friendly vacation rentals in Chesterfield?

Do cottage rentals in Chesterfield have free parking?

Are there vacation rentals with a dedicated workspace in Chesterfield?

Are there family-friendly vacation rentals in Chesterfield?

Do house rentals in Chesterfield have air conditioning?

Destinations to explore