
Holiday rentals with outdoor seating in Chesterfield
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Chesterfield
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

18 Lake Stunning View of Champlain in Adirondacks
Welcome to 18 Lake. Situated in beautiful, quiet, Port Kent, NY, this gem is the perfect place to relax and get away. People come from all across the country to tour this charming 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 vibrant and breathtaking. Fresh maple products are on tap in Spring. Enjoy area attractions such as Ausable Chasm, High Falls Gorge, Port Kent Beach, golf, orchards, hiking and biking.

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.

"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!

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.

4-Season Treehouse @ Bliss Ridge; Best Views in VT
thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Equipped w. a fabulous yotel fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original Dr. Seuss treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works!

Moon Ridge Cabin *Hottub*
Our cabin is a studio with a hot tub & all the amenities. A queen bed, linens, towels, small refrigerator/freezer, microwave, single burner cook plate, dishes, utensils, glassware, pots & pans, toaster & coffee maker. Roku Tv & dvd player with movies. The cabin's bathroom is simular to a cruise ship, you step up into your shower. There is also an private outdoor shower. There is a fire pit with an attached grill & hibachi. We have a garden area & privacy fence between our home & the cabin.

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 Chasm, 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 downtime with family. The apartment has a unique style of its own that will provide you a comfortable and reasonable price place to stay.

Adirondack Mountain Yurt at Blue Pepper Farm
Escape to our 30’ yurt atop a 25-acre pasture with breathtaking views of Whiteface mountain. Accommodating 2 to 6 guests, it’s perfect for family outings or adventures with friends. A winter camping experience: the yurt features basic insulation and is heated by a wood stove, with firewood for purchase on-site. Bring sleeping bags and slippers for warmth in colder temps. Embrace nature’s beauty—plan accordingly, read our reviews, and feel free to ask any questions. Your adventure awaits!

Green Mountain View Private Suite
This one-bedroom private suite offers the full Vermont experience on 12 scenic acres with sweeping Green Mountain views. Enjoy bonfires under the stars, sunrise coffee, and easy access to Shelburne (5 min), Burlington (20 min), Stowe Sugarbush & Bolton Valley Ski Areas (40-60min). Cross-country ski or snowshoe right on the property, and explore nearby hiking, biking, breweries, vineyards & historical sites. Nearby Farm-to-Table restaurants are terrific. High-speed internet and smart TV.

Modern Hot Tub Sauna A-Frame near Whiteface
Welcome to the Black Pine Lodge! Nestled in the heart of the Adirondacks, this modern A-Frame 3 bed/3 bath cabin can accommodate up to 8 guests. Amenities: Hot Tub Panoramic Barrel Sauna Pool Table Helix mattresses Fire Pit Kayaks Surrounded by beautiful trees this place feels tranquil and has lots of hiking trails outside the front door. Explore other hikes, rivers & dining in neighboring Wilmington, Keene and Lake Placid. End the day relaxing at this lodge that caters to all.

Full-body Massage Chair & Hot Tub & Wellness
🎉 Ready for a New Year Reset? 🎉 January rates are lower than usual, making it the perfect time to slow down and start 2026 with clarity at The Place of Prana. If you’re craving a calmer, more intentional start to the year, this stay is designed to help you reset your mind and body. January welcomes new rhythms, soft beginnings, and quiet evenings that make space for fresh energy. Come stay, breathe, and give yourself the reset you deserve for the year ahead.

Porcupine Farm Barn
A converted barn attached to my house, this newly remodeled space is beautiful and inviting. Everything is new and high-end, yet it retains it's barn-y charm. For a couple who are looking to get away in the Adirondacks, this is a unique and appealing option. The house is 3.5 miles from the town of Essex, NY in the Champlain Valley. Gorgeous view of the Green Mountains to the east and farm land all around. The location is convenient to many attractions!
Popular amenities for Chesterfield outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Aunt Shy's Hide-Away

Running Brook

Cozy Mountain House- 50 acres/Trails/Whiteface mnt

Forest Hideaway

Enjoy every season in the Lake Champlain Region

Adirondack Vacation Destination Lodge on Fern Lake

Humble Home Away From Home in the Adirondacks

The Cabin at Pinestone - Adirondacks/Whiteface
Apartment rentals with outdoor seating

Gateway to the Adirondacks on the River “The West”

Cedar View

Downtown Burlington, Renovated, 1 bedroom+

Private, Spacious Retreat...Minutes from Lake!

VT Hideaway studio: breweries,hiking, dogs welcome

Newly renovated one bedroom apartment in Adk mtns

Purple Door Annex

VanHoevenberg Ridge upper level apartment.
Condo rentals with outdoor seating

One level condo in the heart of Stowe Village!

3rd Floor Studio @ The Lodge at Spruce Peak

Ski in/out – Smugglers’ Notch Condo

Lovely Ski-in / Ski-out Studio at “Smuggs”⭐️

Renovated 4-bedroom House: Hot Tub & Outdoor Space

The Château -Luxe condo in heart of downtown Stowe

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

The Cozy Condo at Smuggs Resort!
Quick stats about holiday rentals with outdoor seating in Chesterfield

Total holiday rentals
Explore 60 holiday rentals in Chesterfield

Nightly prices starting at
Chesterfield holiday rentals start at $120 AUD per night before taxes and fees

Verified guest reviews
Over 3,720 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Chesterfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Boston Holiday rentals
- Greater Toronto Area Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Mount Pocono Holiday rentals
- Quebec City Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a fireplace Chesterfield
- Rentals with a kayak Chesterfield
- Waterfront rentals Chesterfield
- Rentals with a patio Chesterfield
- Rentals with lake access Chesterfield
- Rentals with a fire pit Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with beach access Chesterfield
- Pet-friendly rentals Chesterfield
- Family-friendly rentals Chesterfield
- House rentals Chesterfield
- Rentals with outdoor seating Essex County
- Rentals with outdoor seating New York
- Rentals with outdoor seating United States
- Sugarbush Resort
- Parc Safari
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Country Club of Vermont
- Autumn Mountain Winery
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Cozy Cottages & Otter Valley Winery
- Burlington Country Club
- Vermont National Country Club
- Lincoln Peak Vineyard
- Titus Mountain Family Ski Center
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Boyden Valley Winery & Spirits
- North Branch Vineyards




