Photo by Alexandre Ferland

Town of Chesterfield vacation rentals

We found 773 vacation rentals — enter your dates for availability
Discover a selection of 16 homes and other vacation rentals in Town of Chesterfield that are perfect for your trip. Vacation homes offer the best amenities for your stay with friends, family, or just your pet, such as parking and a pool. At the end of the day, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Popular Town of Chesterfield destinations on Vrbo

A frozen waterfall with snow-covered rocks and a bridge in the background.

Keeseville

Keeseville
Keeseville

Holiday rentals with weekly discounts - Town of Chesterfield

Showing deals for:Dec 18 - Dec 25

Image gallery for Adirondack Retreat - Hot Tub & Lake

Terrace/patio
10 out of 10, Exceptional, (48 reviews)
Exceptional
(48 reviews)

Adirondack Retreat - Hot Tub & Lake

Keeseville

8% off
Price is $256
$1,791 for 7 nights
All fees included
Adirondack Retreat - Hot Tub & Lake

Find spaces that suit your style

Find out more about Town of Chesterfield

Book a vacation rental for your Town of Chesterfield getaway

Learn about the unique charm of Town of Chesterfield with a stay in a private vacation home. There's no shortage of things to see and do in the area.Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Sightseeing in and around Town of Chesterfield

Are you looking for attractions to see during your stay? Venture out of your vacation home and experience everything that makes Town of Chesterfield a one-of-a-kind vacation spot. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • ECHO Lake Aquarium and Science Center (12.1 mi / 19.5 km)
  • Shelburne Vineyard (12.6 mi / 20.3 km)
  • Vermont Teddy Bears (12.9 mi / 20.8 km)
  • Bluff Point Golf Resort (13.5 mi / 21.8 km)
  • Snow Farm Vineyard and Winery (14 mi / 22.5 km)
  • Santa's Workshop (19.3 mi / 31 km)

Exploring the natural landscape of Town of Chesterfield

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Town of Chesterfield is a great place to spend some time outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Ausable Chasm (5.3 mi / 8.6 km)
  • North Beach (11.3 mi / 18.2 km)
  • Oakledge Park (11.6 mi / 18.7 km)
  • Red Rocks Park (12 mi / 19.3 km)
  • Waterfront Park (12.1 mi / 19.5 km)
  • Fern Lake (13.1 mi / 21.1 km)

Transportation options to and around Town of Chesterfield

If you'd rather travel by train, the main station is Port Kent Station.

Frequently asked questions

What is the best area to stay in Town of Chesterfield when booking a vacation rental?
Keeseville is among the more popular locations to book a vacation home in Town of Chesterfield. Looking for some top things to do in this destination? Check out Augur Lake and Eagle Mountain Wilderness Preserve.
What is the most popular type of vacation rental accommodation in Town of Chesterfield?
Based on our research, cabins are the most sought-after vacation rental type in Town of Chesterfield. But as you'd expect, everyone's idea of the perfect stay differs. Vrbo has vacation rentals of all shapes and sizes, so you're sure to discover your ideal match.
How much does it cost to rent a vacation rental in Town of Chesterfield?
Length of stay, property type and time of year are among the factors that can affect the price of a vacation home. Simply click on your dates of travel to find your perfect fit. From cozy chalets to sprawling villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Town of Chesterfield?
Prices for beach houses in Town of Chesterfield will vary depending on the size and style of the property and when you're traveling. All you need to do is enter your travel dates into Vrbo and how many guests to view your options and prices. From there you can use our filters to tailor your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Town of Chesterfield?
With 14 properties that welcome pets, your furry best friend can join in on your Town of Chesterfield break. Use the filter tool to search our pet-friendly vacation rentals and find your pawfect pad on Vrbo.
Can I rent a house with a pool in Town of Chesterfield?
Grab your swimwear and inflatable swan, because there are two houses with a private pool in Town of Chesterfield. Unwind at one of these superb vacation homes and every day will be a pool day. Simply enter your dates into Vrbo, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Town of Chesterfield?
Some of the most popular rental amenities guests are looking for in Town of Chesterfield include a water view, a barbecue grill and a garden. Whether you're traveling with friends, family or even pets, Vrbo vacation properties come with the best amenities for making epic memories with your loved ones.
Are there large group vacation rentals in Town of Chesterfield?
Pick from three vacation properties in Town of Chesterfield that can host 10 or more people. Whether you're planning a vacation with extended family or a celebration like a birthday, there's enough space to get your favorite people together under the same roof.
Are there vacation rentals in Town of Chesterfield that welcome kids?
Town of Chesterfield has 14 family-friendly vacation homes. And tracking down a stay that welcomes youngsters is a breeze with Vrbo's "Properties good for families" filter. On top of having the whole place to yourselves, you'll also enjoy access to perks and amenities such as extra bedrooms, pools and kitchens.
What are the top attractions for families in Town of Chesterfield?
If you're on vacation with the kids, make sure you put these family-friendly attractions in Town of Chesterfield on your list of things to see:

  • Augur Lake
  • Port Kent Public Beach Park

Can I find two-bedroom vacation rentals in Town of Chesterfield?
Town of Chesterfield has two two-bedroom properties for you to pick from. Book a vacation home with all the comfort and privacy you need at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Town of Chesterfield?
Pick from seven vacation rentals with WiFi in Town of Chesterfield. If you'd like to disconnect from daily life during your break, but still want to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Town of Chesterfield?
Select your travel dates and then use our filters to find vacation rentals with ac in Town of Chesterfield on Vrbo. With 10 air-conditioned properties on offer here, you can enjoy a cool and comfortable trip.
How old do you have to be to rent a vacation rental in Town of Chesterfield?
You should check with the Town of Chesterfield vacation rental you want on Vrbo as the age limit varies. However, it's typically 16, 18 or 21.
How long can I rent a vacation rental in Town of Chesterfield for?
It really depends on the Town of Chesterfield property. To see a list of options offering extended stays, just type your travel dates and number of people into the Vrbo search page. You can enjoy having the entire property to yourself, as well as amenities such as a full kitchen, air conditioning and a yard to play in. Keep your eyes peeled for long-term stays that offer discounted weekly or monthly prices.
Does Vrbo offer discounts for vacation homes in Town of Chesterfield?
In Town of Chesterfield, you'll find some great discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're planning a short getaway or a few weeks away, we've got a variety of options to suit your needs and budget.

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