Estia Villas - Vacation Rentals in Chester
House
9.2
(
52 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1400 ft²
-
Fireplace/Heating -
Balcony/Terrace -
Pet Friendly -
Kitchen
US $214
/Night
7 Nights - $1,501
9.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
1345.49 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Parking -
Internet
US $332
/Night
7 Nights - $2,326
Hotel
9.8
(
27 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Kitchen
-
Air Conditioner -
Child Friendly
US $138
/Night
7 Nights - $966
House
9.0
(
2 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1344 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $249
/Night
7 Nights - $1,741
New
Bed & Breakfast
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Air Conditioner
-
Internet
-
Laundry
US $75
/Night
7 Nights - $522
House
4 Bedrooms
2 Bathrooms
6 Guests
1270 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $225
/Night
7 Nights - $1,576
House
4 Bedrooms
2 Bathrooms
7 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Air Conditioner
-
Internet
US $216
/Night
7 Nights - $1,512
House
3 Bedrooms
2 Bathrooms
5 Guests
-
Fireplace/Heating
-
Pet Friendly
-
Air Conditioner
-
Internet
US $212
/Night
7 Nights - $1,481
See More Chester Vacation Rentals
Luxury Places to Stay in Chester
Over 52+
Luxury Places to Stay in or Near Chester
Hotel
8.8
(
117 Reviews
)
1 Bathroom
-
Pet Friendly
-
Kitchen
-
Parking
-
Air Conditioner
US $402
/Night
7 Nights - $2,814
2 Bedrooms
2 Bathrooms
3 Guests
1603.82 ft²
-
Fireplace/Heating
-
Pool -
Parking
-
Internet
US $379
/Night
7 Nights - $2,653
Hotel
5.0
(
187 Reviews
)
6 Bathrooms
172.22 ft²
-
Fireplace/Heating
-
Breakfast -
Pet Friendly
-
Parking
US $213
/Night
7 Nights - $1,488
Hotel
8.4
(
104 Reviews
)
4 Bathrooms
292.78 ft²
-
Private Pool -
Hot Tub -
Pool
-
Breakfast
US $191
/Night
7 Nights - $1,338
House
4 Bedrooms
2 Bathrooms
6 Guests
-
Hot Tub
-
Fireplace/Heating
-
Kitchen
-
Parking
US $182
/Night
7 Nights - $1,274
8.7
(
72 Reviews
)
1 Bathroom
301.39 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pet Friendly
-
Parking
US $178
/Night
7 Nights - $1,243
9.0
(
412 Reviews
)
1 Bathroom
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $177
/Night
7 Nights - $1,238
9.8
(
17 Reviews
)
1 Bathroom
-
Child Friendly
-
Laundry
-
Wellness Facilities -
Guest Services
US $174
/Night
7 Nights - $1,217
See More Chester Luxury Vacation Rentals
Find More Chester Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Chester
Over 15+
Top-Rated Vacation Rentals with a Pool in or Near Chester
9.7
(
23 Reviews
)
4 Bathrooms
-
Private Pool
-
Pool
-
Pet Friendly
-
Internet
US $130
/Night
7 Nights - $908
Hotel
8.8
(
838 Reviews
)
1 Bathroom
-
Pool
-
Balcony/Terrace
-
Breakfast
-
Kitchen
US $143
/Night
7 Nights - $998
8.4
(
534 Reviews
)
1 Bathroom
-
Pool
-
Balcony/Terrace
-
Breakfast
-
Kitchen
US $135
/Night
7 Nights - $945
8.2
(
72 Reviews
)
9 Bathrooms
4209.89 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Parking
US $166
/Night
7 Nights - $1,160
8.1
(
286 Reviews
)
1 Bathroom
-
Private Pool
-
Pool
-
Air Conditioner
-
Child Friendly
US $153
/Night
7 Nights - $1,073
7.8
(
204 Reviews
)
6 Bathrooms
396.47 ft²
-
Fireplace/Heating
-
Pool
-
Pet Friendly
-
Parking
US $127
/Night
7 Nights - $887
7.3
(
1044 Reviews
)
2 Bathrooms
3367.76 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $118
/Night
7 Nights - $823
7.1
(
232 Reviews
)
5 Bathrooms
-
Pool
-
Pet Friendly
-
Parking
-
Air Conditioner
US $82
/Night
7 Nights - $575
See More Chester Vacation Rentals with a Pool
Pet-Friendly Vacation Rentals in Chester
Over 8+
Pet-Friendly Vacation Rentals in or Near Chester
House
5.0
(
4 Reviews
)
4 Bedrooms
5 Bathrooms
8 Guests
4000 ft²
-
Balcony/Terrace
-
Pet Friendly
-
Kitchen
-
Air Conditioner
US $510
/Night
7 Nights - $3,570
7.8
(
191 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Balcony/Terrace
-
Breakfast
-
Pet Friendly
US $116
/Night
7 Nights - $813
Hotel
7.0
(
934 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Breakfast
-
Pet Friendly
-
Parking
US $91
/Night
7 Nights - $637
House
2 Bedrooms
3 Bathrooms
6 Guests
-
Hot Tub
-
Fireplace/Heating
-
Pet Friendly
-
Kitchen
US $218
/Night
7 Nights - $1,524
Hotel
7.4
(
117 Reviews
)
8 Bathrooms
355.21 ft²
-
Fireplace/Heating
-
Pet Friendly
-
Parking
-
Air Conditioner
US $114
/Night
7 Nights - $798
Hotel
5.6
(
364 Reviews
)
6 Bathrooms
258.33 ft²
-
Fireplace/Heating
-
Pet Friendly
-
Parking
-
Air Conditioner
US $100
/Night
7 Nights - $702
Hotel
4.5
(
215 Reviews
)
11 Bathrooms
247.57 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Pet Friendly
US $51
/Night
7 Nights - $357
New
1.5
(
2 Reviews
)
3 Bathrooms
301.39 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
View -
Pet Friendly
US $80
/Night
7 Nights - $560
See More Pet-Friendly Vacation Rentals in Chester on PetFriendly.io
Large Vacation Homes & Villas in Chester
Over 1+
Large Vacation Homes & Villas in or Near Chester
House
5 Bedrooms
3 Bathrooms
12 Guests
4500 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $612
/Night
7 Nights - $4,287
See More Family Vacation Rentals in Chester on FVR
Wheelchair Accessible Vacation Homes in Chester
Over 10+
Wheelchair Accessible Vacation Homes in or Near Chester
Hotel
7.7
(
76 Reviews
)
4 Bathrooms
312.16 ft²
-
Fireplace/Heating
-
Breakfast
-
Parking
-
Air Conditioner
US $128
/Night
7 Nights - $898
Hotel
8.4
(
640 Reviews
)
1 Bathroom
-
Kitchen
-
Parking
-
Air Conditioner
-
Internet
US $137
/Night
7 Nights - $959
7.6
(
229 Reviews
)
5 Bathrooms
376.74 ft²
-
Fireplace/Heating
-
Kitchen
-
Parking
-
Air Conditioner
US $116
/Night
7 Nights - $809
8.2
(
961 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Breakfast
-
Kitchen
-
Parking
US $114
/Night
7 Nights - $798
6.4
(
34 Reviews
)
1 Bathroom
3365.51 ft²
-
Oceanfront -
Fireplace/Heating
-
Ocean View -
View
US $113
/Night
7 Nights - $789
Hotel
8.2
(
519 Reviews
)
1 Bathroom
-
Breakfast
-
Kitchen
-
Parking
-
Air Conditioner
US $113
/Night
7 Nights - $790
5.9
(
223 Reviews
)
6 Bathrooms
328.3 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $78
/Night
7 Nights - $548
7.6
(
1000 Reviews
)
1 Bathroom
-
Fireplace/Heating
-
Pool
-
Breakfast
-
Kitchen
US $114
/Night
7 Nights - $798
Chester Vacation Rentals and Airbnb Places to Stay Under $200
Over 12+
Chester Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
5.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
751 ft²
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $140
/Night
7 Nights - $980
6.4
(
232 Reviews
)
3 Bathrooms
319.33 ft²
-
Fireplace/Heating
-
Parking
-
Air Conditioner
-
Internet
US $88
/Night
7 Nights - $614
Hotel
9.0
(
120 Reviews
)
1 Bathroom
-
Parking
-
Air Conditioner
-
Child Friendly
-
Wellness Facilities
US $137
/Night
7 Nights - $960
House
2 Bedrooms
2 Bathrooms
2 Guests
-
Fireplace/Heating
-
Air Conditioner
-
Internet
-
Child Friendly
US $163
/Night
7 Nights - $1,141
House
1 Bedroom
1 Bathroom
2 Guests
-
Fireplace/Heating
-
Kitchen
-
Parking
-
Air Conditioner
US $146
/Night
7 Nights - $1,022
Apartment
1 Bedroom
1 Bathroom
1 Guest
-
Private Pool
-
Pool
-
Air Conditioner
-
Laundry
US $95
/Night
7 Nights - $665
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $142
/Night
7 Nights - $991
Apartment
5.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
6 Guests
-
Kitchen
-
Air Conditioner
-
Child Friendly
-
Bedding/Linens
US $120
/Night
7 Nights - $840
See More Chester Vacation Rental Deals
Instantly Bookable Vacation Homes in Chester
Over 2+
Instantly Bookable Vacation Homes in or Near Chester
House
2 Bedrooms
2 Bathrooms
3 Guests
1608 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $357
/Night
7 Nights - $2,501
House
3 Bedrooms
4 Bathrooms
6 Guests
2200 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $261
/Night
7 Nights - $1,827
See More Chester Short-Term Vacation Rentals
About Chester Vacation Rentals
With more than 61 Chester 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 Chester.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Chester, 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 Chester. Places to stay near Chester are 602.37 ft² on average, with prices averaging US $176 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Chester 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 Chester
| Type | Count |
|---|---|
| Hotels | 37 |
| Vacation Homes | 20 |
| Holiday Apartments | 3 |
| B&B | 1 |
Use these Quick Filters to Find a Vacation Rental in Chester
★ 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 Chester.
Weather in Chester
View the weather forecast for Chester before booking your Chester 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 Chester, VA
Estiavillas offers a large selection of top attractions around Chester. Research things to do on your vacation before you visit Chester.
Iron Bridge Sports Park
Henricus Historical Park
The Lazy Daisy
Dutch Gap Conservation Area
Point of Rocks Park
Presquile National Wildlife Refuge
Parker's Battery Park
Fort Lee
Greater Richmond Convention Center
University of Richmond
Broad Street
Richmond International Raceway
Virginia Commonwealth University
Carytown
Virginia Museum of Fine Arts
Shockoe Slip
Altria Theater
The National
Science Museum of Virginia
Children's Museum of Richmond
Other Places to Stay Near Chester, VA
Woodvale
130 Properties
Iron Bridge Sports Park
77 Properties
Bermuda Hundred
67 Properties
Presquile National Wildlife Refuge
47 Properties
Parker's Battery Park
46 Properties
Henricus Historical Park
45 Properties
Dutch Gap Conservation Area
45 Properties
The Lazy Daisy
43 Properties
Bermuda
35 Properties
Point of Rocks Park
24 Properties
Complexes around Chester, VA
Chester Vacation Rental Frequently Asked Questions
Which vacation homes in Chester are best for families?
If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:
How many vacation rentals are available in Chester?
Currently, the total number of properties listed in 2026 is over 61 in the Chester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chester.
