Chester Villa
650 ft²
4 Guests
3 Bedrooms
1 Bathroom
Ocean View
Cottage
- Ocean View
- Balcony/Terrace
- View
US $241/Night
For 7 Nights US $1,688
818.06 ft²
7 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- View
- Parking
US $333/Night
For 7 Nights US $2,331
US $144/Night
For 7 Nights US $1,006
544 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $376/Night
For 7 Nights US $2,633
3003.13 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- View
- Parking
- Internet
US $321/Night
For 7 Nights US $2,247
16 Guests
6 Bedrooms
6 Bathrooms
Group Friendly
House
US $1,105/Night
For 7 Nights US $7,733
1100 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $336/Night
For 7 Nights US $2,353
3056.95 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $263/Night
For 7 Nights US $1,841
4 Guests
1 Bedroom
1 Bathroom
Couples Retreat
House
- Internet
- Child Friendly
- Barbecue/Outdoor Cooking
US $78/Night
For 7 Nights US $546
2002.09 ft²
6 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Pet Friendly
- Parking
- Internet
US $152/Night
For 7 Nights US $1,064
640 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $182/Night
For 7 Nights US $1,276
US $132/Night
For 7 Nights US $924
Why Choose Rent By Owner for your Chester Villa?
What makes our Villa special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Chester
How to Book Your Chester Villa
What's our booking process?
Our platform allows you to browse a curated selection of villa. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Chester
Common Villa Amenities
What amenities can you expect?
Our Villa are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Chester, MA
Chester Town Hall
Frequently Asked Questions About Chester Rental Villas
1. What are the top Villas in Chester?
There are a lot of options in Chester. If you plan on staying in the Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Villas in Chester:
- 1840's Ship Captain's Farm Estate, 6-10 guests
- Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
- Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath. Sleeps 7.
- Charming Farmhouse - quiet, private & peaceful
- Historic Huntington Home - Walk to Westfield River
- Cozy Modern 4 Bedroom Log Cabin on 45 Secluded Acres in the Berkshires
- Lakes & Leisure: Spacious Berkshire Getaway
- Serene Lakefront Retreat in the Berkshires!
- Cozy Berkshires Vacation Rental Near Hiking!
- Hilltown Nest is a wonderful place for family and friends to gather.
2. How many Villas are available in Chester?
Currently, the total number of properties listed by RBO in 2026 is over 50 in the Chester area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Chester.
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- Fireplace/Heating
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- Balcony/Terrace
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US $382/Night
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1530 ft²
7 Guests
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- Fireplace/Heating
- Balcony/Terrace
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8 Guests
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US $255/Night
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- Fireplace/Heating
- Ocean View
- Balcony/Terrace
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3 Bedrooms
2 Bathrooms
Family Friendly
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- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $343/Night
For 7 Nights US $2,402
1750 ft²
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- Fireplace/Heating
- Ocean View
- Balcony/Terrace
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