1+ Vacation Rentals Near Chestertown |
  1. USA
  2. New York
  3. Lake George
  4. Chestertown

Lakes Resorts - Vacation Rentals in Chestertown

Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/AC & Washer/dryer From US $250
         

9.2 (7 Reviews)
Resort
Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/AC & Washer/dryer
  • Air Conditioner
  • Parking
  • TV

View Availability
See More Chestertown Vacation Rentals

Luxury Places to Stay in Chestertown

Over 170+ Luxury Places to Stay in or Near Chestertown
Spectacular Lakefront Cabin on 12 acres on Friends Lake From US $1,098
         

9.8 (15 Reviews)
Cabin
Spectacular Lakefront Cabin on 12 acres on Friends Lake
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Unique Lakefront House with Sandy Beach and Dock - Sweeping Views From US $943
         

8.6 (4 Reviews)
House
Unique Lakefront House with Sandy Beach and Dock - Sweeping Views
  • Parking
  • View
  • Ocean View

View Availability
Lakefront home steps away from a private, gentle sloping sandy beach & fire pit. From US $899
         

10.0 (43 Reviews)
House
Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
  • Air Conditioner
  • Parking
  • TV

View Availability
Mimi’s by the lake From US $788
         

9.8 (13 Reviews)
House
Mimi’s by the lake
  • Air Conditioner
  • Parking
  • TV

View Availability
Forest Lake Haven close to Lake George and Gore Mountain, 5 BR spacious and NEW From US $761
         

10.0 (1 Review)
House
Forest Lake Haven close to Lake George and Gore Mountain, 5 BR spacious and NEW
  • Air Conditioner
  • Parking
  • TV

View Availability
WaterFront Adirondack Home-located between Gore and Lake George From US $745
         

10.0 (12 Reviews)
House
WaterFront Adirondack Home-located between Gore and Lake George
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Lakefront Home - 20 Min from Gore Mountain w/Hot Tub From US $716
         

10.0 (10 Reviews)
House
Lakefront Home - 20 Min from Gore Mountain w/Hot Tub
  • Air Conditioner
  • Parking
  • TV

View Availability
Luxury Adirondack getaway with 4 private ensuites From US $694
         

New
Condo
Luxury Adirondack getaway with 4 private ensuites
  • Parking
  • TV
  • View

View Availability
See More Chestertown Luxury Vacation Rentals
Find More Chestertown Villas, Resorts, & Rentals on BedroomVillas

Top-Rated Vacation Rentals with a Pool in Chestertown

Over 18+ Top-Rated Vacation Rentals with a Pool in or Near Chestertown
Eagles Nest at Loon Lake near Gore Mountain From US $505
         

10.0 (113 Reviews)
House
Eagles Nest at Loon Lake near Gore Mountain
  • Air Conditioner
  • Parking
  • Pool

View Availability
Modern Cabin w/Hot Tub-Minutes to Lakes & Skiing From US $373
         

10.0 (36 Reviews)
Cabin
Modern Cabin w/Hot Tub-Minutes to Lakes & Skiing
  • Air Conditioner
  • Parking
  • Pool

View Availability
Fairview Cabin, Pool, True Adirondack Cabin steps from Loon Lake From US $316
         

10.0 (13 Reviews)
House
Fairview Cabin, Pool, True Adirondack Cabin steps from Loon Lake
  • Parking
  • Pool
  • TV

View Availability
Chalet Cabin, Gore Skiing, Pool, AC, Spacious Cabin, Loon Lake From US $387
         

10.0 (12 Reviews)
House
Chalet Cabin, Gore Skiing, Pool, AC, Spacious Cabin, Loon Lake
  • Air Conditioner
  • Parking
  • Pool

View Availability
Cozy 3BR 3.5BA Lodge w/Lake & Beach Access, Screened in Patio, Grill, Sunroom From US $460
         

10.0 (2 Reviews)
Cabin
Cozy 3BR 3.5BA Lodge w/Lake & Beach Access, Screened in Patio, Grill, Sunroom
  • Air Conditioner
  • Parking
  • Pool

View Availability
Log Haven Cabin, Gore Skiing, Pool/AC/Fireplace, Steps to Loon Lake From US $311
         

9.8 (21 Reviews)
Cabin
Log Haven Cabin, Gore Skiing, Pool/AC/Fireplace, Steps to Loon Lake
  • Air Conditioner
  • Parking
  • Pool

View Availability
Sleepy Hollow, Gore Mountain, Pool, AC, Fireplace, close to Loon Lake From US $391
         

9.8 (7 Reviews)
House
Sleepy Hollow, Gore Mountain, Pool, AC, Fireplace, close to Loon Lake
  • Air Conditioner
  • Parking
  • Pool

View Availability
Lily Pad North at Loon Lake near Gore Mountain From US $219
         

9.6 (30 Reviews)
Apartment
Lily Pad North at Loon Lake near Gore Mountain
  • Air Conditioner
  • Parking
  • Pool

View Availability
See More Chestertown Vacation Rentals with a Pool

Pet-Friendly Vacation Rentals in Chestertown

Over 35+ Pet-Friendly Vacation Rentals in or Near Chestertown
A beautiful lake view cabin on Friends Lake From US $228
         

9.6 (53 Reviews)
Cottage
A beautiful lake view cabin on Friends Lake
  • Parking
  • Pet Friendly
  • TV

View Availability
Solitude at Lake's End From US $189
         

|
New
House
Solitude at Lake's End
  • Parking
  • Pet Friendly
  • Balcony/Terrace

View Availability
Elizabeth. A Guest House Near Lake George. From US $562
         

8.2 (45 Reviews)
House
Elizabeth. A Guest House Near Lake George.
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming! From US $205
         

8.6 (10 Reviews)
Cottage
#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
  • Parking
  • Pet Friendly
  • TV

View Availability
Secluded and Cozy Townhome at Tripp Lake From US $183
         

10.0 (104 Reviews)
House
Secluded and Cozy Townhome at Tripp Lake
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Peaceful retreat in the heart of the Adirondacks. From US $272
         

10.0 (15 Reviews)
House
Peaceful retreat in the heart of the Adirondacks.
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront From US $225
         

10.0 (4 Reviews)
Cottage
#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront
  • Parking
  • Pet Friendly
  • TV

View Availability
40 acre-Lakefront ADK home From US $572
         

9.8 (58 Reviews)
House
40 acre-Lakefront ADK home
  • Parking
  • Pet Friendly
  • TV

View Availability
See More Pet-Friendly Vacation Rentals in Chestertown on PetFriendly.io

Large Vacation Homes & Villas in Chestertown

Over 30+ Large Vacation Homes & Villas in or Near Chestertown
Serene Loon Lake Waterfront - Sleeps up to 10 From US $573
         

10.0 (7 Reviews)
House
Serene Loon Lake Waterfront - Sleeps up to 10
  • Air Conditioner
  • Parking
  • TV

View Availability
The Fern Lodge From US $599
         

|
10.0 (2 Reviews)
Bed & Breakfast
The Fern Lodge
  • Air Conditioner
  • Parking
  • View

View Availability
4 Mi to Beach & Lake: Spacious Home in Chestertown From US $337
         

10.0 (2 Reviews)
House
4 Mi to Beach & Lake: Spacious Home in Chestertown
  • Air Conditioner
  • Parking
  • TV

View Availability
Start your Adirondack escape at Cape Cotter! Near Gore Mountain and Lake George! From US $620
         

10.0 (1 Review)
House
Start your Adirondack escape at Cape Cotter! Near Gore Mountain and Lake George!
  • Air Conditioner
  • Parking
  • TV

View Availability
30 acre-ADK Log Cabin on Kelm Lake From US $479
         

9.6 (41 Reviews)
House
30 acre-ADK Log Cabin on Kelm Lake
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
The Lily Pad at Loon Lake near Gore Mountain From US $387
         

9.6 (39 Reviews)
House
The Lily Pad at Loon Lake near Gore Mountain
  • Air Conditioner
  • Parking
  • TV

View Availability
Large Cozy House in the Woods From US $592
         

9.4 (9 Reviews)
House
Large Cozy House in the Woods
  • Air Conditioner
  • Parking
  • TV

View Availability
Lakefront cabin with beautiful loft, game room, views, private dock From US $509
         

9.2 (48 Reviews)
House
Lakefront cabin with beautiful loft, game room, views, private dock
  • Parking
  • TV
  • View

View Availability
See More Family Vacation Rentals in Chestertown on FVR

Wheelchair Accessible Vacation Homes in Chestertown

Over 6+ Wheelchair Accessible Vacation Homes in or Near Chestertown
Family-friendly log cabin with sandy beach, kayaks, near Lake George From US $496
         

5.0 (11 Reviews)
Ski Chalet
Family-friendly log cabin with sandy beach, kayaks, near Lake George
  • Air Conditioner
  • TV
  • Wheelchair Accessible

View Availability
Pine's Way Camp From US $348
         

|
9.0 (5 Reviews)
House
Pine's Way Camp
  • View
  • Wheelchair Accessible
  • Private Beach

View Availability
Basic Adirondack Camp From US $375
         

|
9.0 (2 Reviews)
House
Basic Adirondack Camp
  • Pet Friendly
  • Wheelchair Accessible
  • Balcony/Terrace

View Availability
Private Contemporary From US $525
         

|
New
House
Private Contemporary
  • View
  • Wheelchair Accessible
  • Private Beach

View Availability
Lakeside Vibes From US $407
         

|
New
House
Lakeside Vibes
  • View
  • Wheelchair Accessible
  • Private Beach

View Availability
Hunerburg White House From US $330
         

|
New
House
Hunerburg White House
  • View
  • Wheelchair Accessible
  • Balcony/Terrace

View Availability
See More Properties

Chestertown Varoom and Airbnb Places to Stay Under $200

Over 24+ Chestertown Varoom and Airbnb Places to Stay Under $200
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming! From US $172
         

9.6 (12 Reviews)
Cottage
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
  • Parking
  • Pet Friendly
  • TV

View Availability
Between the Pines - Unit A From US $166
         

|
9.3 (8 Reviews)
Apartment
Between the Pines - Unit A
  • Air Conditioner
  • View
  • Private Beach

View Availability
Pine Tree Motel & Cabins From US $194
         

9.2 (146 Reviews)
Hotel
Pine Tree Motel & Cabins
  • Air Conditioner
  • Parking
  • Pool

View Availability
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming! From US $179
         

9.4 (18 Reviews)
Cottage
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
  • Parking
  • Pet Friendly
  • TV

View Availability
Cozy retreat with fireplace, kayaks, and shared beach/pond access From US $141
         

8.8 (22 Reviews)
Condo
Cozy retreat with fireplace, kayaks, and shared beach/pond access
  • Parking
  • TV
  • View

View Availability
#3 Chester @ Birchwood Cottages at Loon Lake. Family Friendly Waterfront From US $179
         

8.4 (6 Reviews)
Cottage
#3 Chester @ Birchwood Cottages at Loon Lake. Family Friendly Waterfront
  • Parking
  • Pet Friendly
  • TV

View Availability
Secluded and Cozy Lakeside Townhome on Tripp Lake! From US $166
         

New
House
Secluded and Cozy Lakeside Townhome on Tripp Lake!
  • Parking
  • Pet Friendly
  • TV

View Availability
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains From US $200
         

9.6 (25 Reviews)
Cabin
Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
See More Chestertown Vacation Rental Deals

Instantly Bookable Vacation Homes in Chestertown

Over 62+ Instantly Bookable Vacation Homes in or Near Chestertown
Lakefront cabin with beautiful views, lake and beach access From US $231
         

9.6 (13 Reviews)
House
Lakefront cabin with beautiful views, lake and beach access
  • Parking
  • TV
  • View

View Availability
TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories! From US $367
         

10.0 (109 Reviews)
House
TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
  • Parking
  • TV
  • View

View Availability
Loon Lake, Chestertown - Spotless, bright chalet, sleeps 6-8, near public beach From US $371
         

10.0 (85 Reviews)
Ski Chalet
Loon Lake, Chestertown - Spotless, bright chalet, sleeps 6-8, near public beach
  • Air Conditioner
  • Parking
  • TV

View Availability
Welcome home! From US $333
         

10.0 (69 Reviews)
House
Welcome home!
  • Air Conditioner
  • Parking
  • TV

View Availability
Rustic Adirondack Retreat on Tripp Lake From US $291
         

10.0 (46 Reviews)
House
Rustic Adirondack Retreat on Tripp Lake
  • Air Conditioner
  • Parking
  • TV

View Availability
NEW for 2024, 6 person hot tub. Spacious country home with large back yard. From US $278
         

10.0 (22 Reviews)
House
NEW for 2024, 6 person hot tub. Spacious country home with large back yard.
  • Air Conditioner
  • Parking
  • TV

View Availability
Private Adirondack lakefront Cottage on Loon Lake From US $208
         

10.0 (12 Reviews)
Cottage
Private Adirondack lakefront Cottage on Loon Lake
  • Parking
  • TV
  • View

View Availability
21 Mi to Gore Mtn: Adirondack Oasis w/Sauna From US $397
         

10.0 (5 Reviews)
House
21 Mi to Gore Mtn: Adirondack Oasis w/Sauna
  • Air Conditioner
  • Parking
  • TV

View Availability
See More Chestertown Short-Term Vacation Rentals

About Chestertown Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Lakesresorts Chestertown, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chestertown. Places to stay near Chestertown are 800 ft² on average, with prices averaging $250 a night.

Lakesresorts makes it easy and safe to find and compare vacation rentals in Chestertown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Chestertown

Type Count
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Chestertown

★ Pro Tip: Lakesresorts makes it easy to compare the best listings on Lakesresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Lakesresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chestertown.

Weather in Chestertown

View the weather forecast for Chestertown before booking your Chestertown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chestertown, NY

Lakesresorts offers a large selection of top attractions around Chestertown. Research things to do on your vacation before you visit Chestertown.


Friends Lake Loon Lake Beach Tripp Pond Loon Lake Gore Mountain Ski Resort Outlets at Lake George Great Escape and Splashwater Kingdom Fort William Henry West Mountain Ski Resort Million Dollar Beach Lake George Dog Beach Shepard's Beach Park Lake George Steamboat Company Adirondack Outlet Mall Cool Insuring Arena Lake George Shoreline Cruises Magic Forest Family Fun Park Charles R. Wood Theater Hickory Ski Center Wild West Ranch and Western Town

Other Places to Stay Near Chestertown, NY


Friends Lake Inn 129 Properties Loon Lake Beach 129 Properties Chester Shores 127 Properties Loon Lake 106 Properties Friends Lake 99 Properties Tripp Pond 56 Properties