A stone bridge over a river with a waterfall and a small building on the right.

Photo by Alexandre Ferland

Town of Chesterfield holiday rentals

We found 772 holiday rentals — enter your dates for availability

Discover a selection of 16 homes and other holiday rentals in Town of Chesterfield that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as Wi-Fi and cable TV. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Popular Town of Chesterfield destinations on Stayz

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

Keeseville

Holiday rentals with weekly discounts – Town of Chesterfield

Showing deals for:11 Dec - 18 Dec

Have coffee or tea at 2 high seat bar in screened in porch/ entryway/ mud room.

Exceptional

(61 reviews)

Wagner’s Camp 4 beds 2 bath

Jay

7% off

AU$3,565

for 7 nights, 1 cabin

AU$509 per night

includes taxes & fees

Very well stock kitchen with high quality cookware and tools

Large ADK style living room with stone fireplace, antler chandelier and canoe

Exceptional

(41 reviews)

Luxury meets Rustic- Beautiful Lodge 1.9 miles from Whiteface-EV charger

Wilmington

8% off

AU$7,678

for 7 nights, 1 home

AU$1,097 per night

includes taxes & fees

Exceptional

(70 reviews)

Best View on Malletts Bay

Colchester

8% off

AU$8,103

for 7 nights, 1 home

AU$1,158 per night

includes taxes & fees

Enjoy delicious meals in the kitchen and let the dishwasher do the clean up!

Exceptional

(48 reviews)

Adirondack Retreat - Hot Tub & Lake

Keeseville

8% off

AU$2,707

for 7 nights, 1 cabin

AU$387 per night

includes taxes & fees

Exceptional

(19 reviews)

Charming & Convenient 6 Bedroom Mountainside Lodge

Elizabethtown

11% off

AU$8,256

for 7 nights, 1 home

AU$1,179 per night

includes taxes & fees

Exceptional

(118 reviews)

Mountain Side Home With Absolutely Stunning Adirondack Mountain Views

Wilmington

7% off

AU$5,922

for 7 nights, 1 home

AU$846 per night

includes taxes & fees

Exceptional

(252 reviews)

Log Cabin on the Ausable River

Keene

8% off

AU$2,244

for 7 nights, 1 cabin

AU$321 per night

includes taxes & fees

Exceptional

(49 reviews)

Enjoy all the Adirondacks have to offer!

Jay

8% off

AU$2,816

for 7 nights, 1 chalet

AU$402 per night

includes taxes & fees

Exceptional

(30 reviews)

Secluded Hillside Home With Views of Whiteface

Keene

12% off

AU$7,440

for 7 nights, 1 home

AU$1,063 per night

includes taxes & fees

Exceptional

(78 reviews)

Whiteface Mountain Views From Serene Farm House

Au Sable Forks

7% off

AU$3,741

for 7 nights, 1 home

AU$534 per night

includes taxes & fees

Exceptional

(21 reviews)

Lakehouse Family Getaway.

Colchester

8% off

AU$8,634

for 7 nights, 1 home

AU$1,233 per night

includes taxes & fees

Wonderful

(36 reviews)

Lakeside Luxury

Plattsburgh

7% off

AU$6,732

for 7 nights, 1 home

AU$962 per night

includes taxes & fees

Exceptional

(20 reviews)

City Center Sanctuary

Burlington

8% off

AU$11,811

for 7 nights, 1 home

AU$1,687 per night

includes taxes & fees

Wonderful

(19 reviews)

Woodland Vacations Little Bear

Wilmington

8% off

AU$2,763

for 7 nights, 1 home

AU$395 per night

includes taxes & fees

Exceptional

(42 reviews)

Authentic Log Cabin, Secluded Site on the Ausable River

Jay

9% off

AU$3,389

for 7 nights, 1 cabin

AU$484 per night

includes taxes & fees

Very good

(16 reviews)

4 Bedroom 2 Bathroom Entire Home with Walk-In Lake Access

Plattsburgh

7% off

AU$3,834

for 7 nights, 1 home

AU$548 per night

includes taxes & fees

Exceptional

(24 reviews)

New Home in Burlington

Burlington

7% off

AU$5,300

for 7 nights, 1 home

AU$757 per night

includes taxes & fees

Very good

(22 reviews)

Private Home Food + Bars

Winooski

12% off

AU$3,326

for 7 nights, 1 home

AU$475 per night

includes taxes & fees

Exceptional

(14 reviews)

River Rock Chalet, in-law suite with private entrance, 2 bedrooms and 2 baths.

Jay

7% off

AU$3,205

for 7 nights, 1 room

AU$458 per night

includes taxes & fees

Screen Porch, Brick Patio, Deck, Outdoor Table and Chairs

Exercise Room - 50" TV, Concept 2 Rower and DYNO, Soloflex, Bowflex, SkiersEdge

Exceptional

(78 reviews)

Newly Updated Large Home, Walk Downtown, UVM & Hospital ~ Includes Bicycles!

Burlington

19% off

AU$10,945

for 7 nights, 1 home

AU$1,564 per night

includes taxes & fees

LIVING ROOM 2 Queen Hide-a-Beds with Spring Mattresses, pre-made - ready to use

BEDROOM 2 Queen Size Posturepedic Bed 1000 count Cotton Sheets and Blankets

Exceptional

(44 reviews)

Newly Updated Cozy Home ~ Located Downtown, UVM, Hospital Includes 8 Bikes!

Burlington

19% off

AU$3,077

for 7 nights, 1 home

AU$440 per night

includes taxes & fees

Exceptional

(54 reviews)

Private New House | Food + Bars + Downtown

Winooski

8% off

AU$4,796

for 7 nights, 1 home

AU$685 per night

includes taxes & fees

Exceptional

(38 reviews)

Quiet Vaulted Private Home, heart of popular south end.

Burlington

20% off

AU$4,082

for 7 nights, 1 home

AU$583 per night

includes taxes & fees

View from the kitchen looking back into the living room

Custom live edge kitchen table which provides adequate and comfortable seating

Exceptional

(54 reviews)

Whiteface Wilmington Cottage Level 2 EV charger~Hot tub-Fireplace-Dog friendly

Wilmington

8% off

AU$3,091

for 7 nights, 1 home

AU$442 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Town of Chesterfield

Cozy 2-bedroom cabin in charming Keeseville with access to private Augur lake

Sleeps 6 · 2 bedrooms · 1 bathroom

Premier Host

Family fun at This Beautiful Lakefront Adirondack Camp

Sleeps 8 · 3 bedrooms · 2 bathrooms

Charming 3-bedroom house in Keeseville

Sleeps 7 · 3 bedrooms · 1+ bathroom

Adirondack family Lakehouse 5 min driving from Ausable chasm.

Sleeps 8 · 4 bedrooms · 3+ bathrooms

Premier Host

Architects Dream Home Overlooking Picturesque Lake Champlain

Sleeps 8 · 3 bedrooms · 2 bathrooms

Premier Host

Enjoy Modern Amenities and Fun on the Water with Kayaks & Paddle Boat

Sleeps 6 · 3 bedrooms · 2 bathrooms

Book a holiday rental for your Town of Chesterfield getaway

Learn about the unique charm of Town of Chesterfield with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Town of Chesterfield

Do you want to find top things to see and do while you're in town? Venture out of your holiday home and experience everything that makes Town of Chesterfield a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

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 an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Town of Chesterfield. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

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)

Transport options to and around Town of Chesterfield

If you prefer train travel, the main station is Port Kent Station.

Frequently asked questions

What is the most popular type of holiday home accommodation in Town of Chesterfield?

According to our research, houses are considered the most popular type of holiday property in Town of Chesterfield. But of course, everyone's idea of an awesome trip can differ. Stayz has holiday homes with every shape, size and budget in mind, and we'll help you find your ideal fit.

How much does it cost to rent a holiday home in Town of Chesterfield?

A range of things can influence the price of a holiday home in Town of Chesterfield, such as the length of stay, season and type of property. However, all our holiday homes have something in common — incredible value. Simply enter your travel dates to find your ideal match.

How much does it cost to rent a beach house in Town of Chesterfield?

The average price for a holiday home near the beach in Town of Chesterfield depends on when you'll be there and the size and style of property you want. You can find prices easily and quickly on Stayz by entering your destination and preferred travel dates. Then use our filters to pick the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a pool.

Are there pet-friendly holiday homes in Town of Chesterfield?

Yes. There are. You can pick from 14 holiday homes that allow pets in Town of Chesterfield. Lots of our pet-friendly holiday homes have an outdoor space for your furry friend to run around in, dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Stayz.

Can I rent a house with a pool in Town of Chesterfield?

Grab your swimming gear and inflatable swan, because there are two houses with a private pool in Town of Chesterfield. Settle in at one of these popular holiday homes and make every day a pool day. Simply enter your dates into Stayz, then check the "pool" filter to find the perfect place for a splashing good time!

What are popular home amenities in Town of Chesterfield?

A lake view, a garden and a nearby waterfront are the most popular home amenities in Town of Chesterfield. Whether you're heading away by yourself, with your spouse or a group of best friends, Stayz will help you find a holiday home that suits your style with a load of extras you'll love.

Are there large group holiday homes in Town of Chesterfield?

You'll find three holiday homes in Town of Chesterfield that can accommodate a group of 10 or more guests. Whether you're organising time away with the family or a celebration like a birthday, there's plenty of space to get your loved ones together under one roof.

Are there holiday homes in Town of Chesterfield that welcome kids?

With 14 family-friendly holiday homes to select from in Town of Chesterfield, now is a great time to introduce the little ones to the excitement of travel. Check our "Properties good for families" filter box to find stays packed with conveniences ideal for families on the move, like living rooms, patios, bunk beds and hot tubs.

What are the top attractions for families in Town of Chesterfield?

Keeping the kids amused during your holiday in Town of Chesterfield is easy with these cool family-friendly attractions:

Port Kent Public Beach Park
Augur Lake
Oldham Theatre

Can I find two-bedroom holiday homes in Town of Chesterfield?

Gather your loved ones and relax in total privacy and comfort in one of the two two-bedroom holiday homes Town of Chesterfield has to offer.

Are there holiday homes with WiFi in Town of Chesterfield?

There are seven holiday homes with WiFi in Town of Chesterfield. If you'd like to disconnect from the world during your break, but still need to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Stayz.

How can I find holiday homes with air conditioning in Town of Chesterfield?

Town of Chesterfield has 10 holiday homes where you'll be able to unwind in air-conditioned comfort. To book a property on Stayz that has this perk, enter your desired travel dates and use the filters to select the "air conditioning" box.

How old do you have to be to rent a holiday home in Town of Chesterfield?

You should check with the Town of Chesterfield holiday home you'd like on Stayz as the minimum age varies. However, it's generally 16, 18 or 21.

How long can I rent a holiday home in Town of Chesterfield for?

The amount of time you can stay in a Town of Chesterfield holiday home for depends on the property. Just enter your preferred travel dates to see options that offer long-term stays. They have all you require to make your extended holiday more convenient and enjoyable, such as laundries and air conditioning. Some Stayz holiday homes may also offer weekly or monthly discounts, so you can stay longer for less money.

More holiday ideas

Holiday homes