Estia Villas - Vacation Rentals in Chestertown
Cottage
9.6
(
53 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking -
Balcony/Terrace -
Kitchen -
Internet
US $261
/Night
7 Nights - $1,826
House
3 Bedrooms
2 Bathrooms
6 Guests
1399.31 ft²
-
Parking
-
Balcony/Terrace
-
Internet
-
Pet Friendly
US $189
/Night
7 Nights - $1,323
Bed & Breakfast
9.8
(
57 Reviews
)
1 Bedroom
1 Bathroom
-
Hot Tub -
Breakfast -
Parking
-
Spa
US $549
/Night
7 Nights - $3,846
House
8.4
(
51 Reviews
)
6 Bedrooms
3 Bathrooms
18 Guests
4000 ft²
-
Private Pool -
Parking
-
Pool -
Ocean View
US $485
/Night
7 Nights - $3,393
House
9.6
(
13 Reviews
)
1 Bedroom
2 Bathrooms
2 Guests
519 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $257
/Night
7 Nights - $1,802
Cottage
8.6
(
10 Reviews
)
4 Bedrooms
1 Bathroom
6 Guests
500 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $230
/Night
7 Nights - $1,607
House
10.0
(
121 Reviews
)
7 Bedrooms
4 Bathrooms
22 Guests
3229 ft²
-
Oceanfront -
Parking
-
Ocean View
-
Balcony/Terrace
US $761
/Night
7 Nights - $5,330
House
10.0
(
109 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $373
/Night
7 Nights - $2,611
See More Chestertown Vacation Rentals
Luxury Places to Stay in Chestertown
Over 158+
Luxury Places to Stay in or Near Chestertown
Cabin
9.8
(
17 Reviews
)
5 Bedrooms
4 Bathrooms
20 Guests
3500 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,426
/Night
7 Nights - $9,984
House
10.0
(
2 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
4000 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,166
/Night
7 Nights - $8,159
House
10.0
(
45 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1512 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,013
/Night
7 Nights - $7,090
House
9.8
(
14 Reviews
)
6 Bedrooms
3 Bathrooms
12 Guests
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $976
/Night
7 Nights - $6,830
Cabin
9.8
(
6 Reviews
)
3 Bedrooms
2 Bathrooms
9 Guests
2250 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $818
/Night
7 Nights - $5,726
House
10.0
(
7 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $787
/Night
7 Nights - $5,509
House
8.8
(
11 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
3000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $772
/Night
7 Nights - $5,402
House
10.0
(
15 Reviews
)
4 Bedrooms
2 Bathrooms
14 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $761
/Night
7 Nights - $5,326
See More Chestertown Luxury Vacation Rentals
Find More Chestertown Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Chestertown
Over 17+
Top-Rated Vacation Rentals with a Pool in or Near Chestertown
Cabin
10.0
(
42 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2000 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $419
/Night
7 Nights - $2,932
House
10.0
(
13 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
900 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $407
/Night
7 Nights - $2,849
House
10.0
(
12 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1052 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $451
/Night
7 Nights - $3,155
Other
10.0
(
8 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
1450 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $649
/Night
7 Nights - $4,545
Cabin
10.0
(
3 Reviews
)
3 Bedrooms
3 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $663
/Night
7 Nights - $4,639
Apartment
9.8
(
31 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1076 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
View
US $181
/Night
7 Nights - $1,264
House
9.8
(
7 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1000 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $476
/Night
7 Nights - $3,329
Cabin
9.6
(
22 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
585 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $367
/Night
7 Nights - $2,568
Pet-Friendly Vacation Rentals in Chestertown
Over 29+
Pet-Friendly Vacation Rentals in or Near Chestertown
House
10.0
(
62 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
2500 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $638
/Night
7 Nights - $4,469
House
9.8
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2002.09 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $422
/Night
7 Nights - $2,954
House
10.0
(
18 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $361
/Night
7 Nights - $2,529
New
Cabin
10.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $453
/Night
7 Nights - $3,174
House
9.8
(
57 Reviews
)
4 Bedrooms
3 Bathrooms
14 Guests
3500 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $678
/Night
7 Nights - $4,744
House
9.8
(
34 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
2000 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
View
US $336
/Night
7 Nights - $2,354
House
9.6
(
42 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
2200 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $569
/Night
7 Nights - $3,982
House
9.6
(
7 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1200 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $240
/Night
7 Nights - $1,682
See More Pet-Friendly Vacation Rentals in Chestertown on PetFriendly.io
Large Vacation Homes & Villas in Chestertown
Over 31+
Large Vacation Homes & Villas in or Near Chestertown
House
10.0
(
1 Review
)
4 Bedrooms
2 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $617
/Night
7 Nights - $4,318
Bed & Breakfast
10.0
(
2 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
508.06 ft²
-
Breakfast
-
EV Charge Station -
Parking
-
Skiing
US $528
/Night
7 Nights - $3,696
House
9.6
(
42 Reviews
)
4 Bedrooms
2 Bathrooms
11 Guests
1991 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $383
/Night
7 Nights - $2,681
House
9.4
(
53 Reviews
)
5 Bedrooms
3 Bathrooms
10 Guests
1568 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $524
/Night
7 Nights - $3,666
House
9.4
(
10 Reviews
)
3 Bedrooms
3 Bathrooms
13 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $659
/Night
7 Nights - $4,615
House
8.8
(
15 Reviews
)
5 Bedrooms
2 Bathrooms
13 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $666
/Night
7 Nights - $4,659
Cabin
6 Bedrooms
3 Bathrooms
12 Guests
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $651
/Night
7 Nights - $4,555
New
House
3 Bedrooms
3 Bathrooms
10 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $480
/Night
7 Nights - $3,362
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
Ski Chalet
5.0
(
11 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1500 ft²
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $496
/Night
7 Nights - $3,475
House
9.3
(
4 Reviews
)
4 Bedrooms
2 Bathrooms
6 Guests
2023.62 ft²
-
Private Beach -
Skiing
-
Ocean View
-
Balcony/Terrace
US $283
/Night
7 Nights - $1,980
House
9.0
(
2 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
742.71 ft²
-
Skiing
-
Balcony/Terrace
-
Pet Friendly
-
Child Friendly
US $375
/Night
7 Nights - $2,625
House
1 Bedroom
2 Bathrooms
8 Guests
1420.84 ft²
-
Private Beach
-
Oceanfront
-
Skiing
-
Ocean View
US $525
/Night
7 Nights - $3,675
House
3 Bedrooms
1 Bathroom
4 Guests
904.17 ft²
-
Private Beach
-
Oceanfront
-
Skiing
-
Ocean View
US $407
/Night
7 Nights - $2,849
House
1 Bedroom
1 Bathroom
6 Guests
1280.91 ft²
-
Skiing
-
Balcony/Terrace
-
View
-
Child Friendly
US $330
/Night
7 Nights - $2,310
Chestertown Vacation Rentals and Airbnb Places to Stay Under $200
Over 17+
Chestertown Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
9.8
(
50 Reviews
)
2 Bedrooms
1 Bathroom
5 Guests
893 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $181
/Night
7 Nights - $1,264
Apartment
9.3
(
8 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
764.24 ft²
-
Private Beach
-
Skiing
-
Ocean View
-
View
US $166
/Night
7 Nights - $1,162
US $194
/Night
7 Nights - $1,360
Cottage
8.4
(
6 Reviews
)
3 Bedrooms
2 Bathrooms
5 Guests
400 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $197
/Night
7 Nights - $1,377
House
9.6
(
10 Reviews
)
5 Bedrooms
2 Bathrooms
10 Guests
1800 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $178
/Night
7 Nights - $1,248
House
10.0
(
11 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
-
Oceanfront
-
Breakfast
-
Parking
-
Ocean View
US $200
/Night
7 Nights - $1,400
Condo
9.6
(
10 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
1440 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $127
/Night
7 Nights - $887
Condo
9.4
(
21 Reviews
)
1 Bedroom
2 Bathrooms
4 Guests
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $145
/Night
7 Nights - $1,015
See More Chestertown Vacation Rental Deals
Instantly Bookable Vacation Homes in Chestertown
Over 50+
Instantly Bookable Vacation Homes in or Near Chestertown
House
10.0
(
72 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1660 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $380
/Night
7 Nights - $2,661
House
10.0
(
47 Reviews
)
3 Bedrooms
1 Bathroom
7 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $333
/Night
7 Nights - $2,331
House
10.0
(
23 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $388
/Night
7 Nights - $2,716
Cottage
10.0
(
15 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
946 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $272
/Night
7 Nights - $1,906
House
10.0
(
12 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $382
/Night
7 Nights - $2,677
New
House
10.0
(
5 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1720 ft²
-
Parking
-
Spa
-
Balcony/Terrace
-
Kitchen
US $478
/Night
7 Nights - $3,346
House
10.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1900 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $517
/Night
7 Nights - $3,616
House
10.0
(
1 Review
)
3 Bedrooms
3 Bathrooms
7 Guests
3000 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $582
/Night
7 Nights - $4,073
About Chestertown Vacation Rentals
With more than 167 Chestertown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chestertown.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas 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 1149.92 ft² on average, with prices averaging US $426 a night.
Estiavillas 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 |
|---|---|
| Vacation Homes | 109 |
| Cabin Rentals | 21 |
| Cottages | 7 |
| Holiday Apartments | 5 |
| Ski Chalet Rentals | 5 |
| Hotels | 4 |
| B&B | 2 |
| Others | 2 |
Use these Quick Filters to Find a Vacation Rental in Chestertown
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas 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
Estiavillas 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
Chestertown Vacation Rental Frequently Asked Questions
Which vacation homes in Chestertown are best for families?
If you are looking for a family-friendly vacation home in Chestertown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chestertown:
How many vacation rentals are available in Chestertown?
Currently, the total number of properties listed in 2026 is over 167 in the Chestertown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chestertown.
