Best Vacation Homes in Chester
Cottage
10.0(48 Reviews)
3 Bedrooms
1 Bath
4 Guests
650 ft²
Ocean View
Balcony/Terrace
View
Kitchen
US $277/Night
7 Nights - US $1,937
House
8.0(1 Review)
2 Bedrooms
1 Bath
7 Guests
818.06 ft²
Fireplace/Heating- View
Parking
Internet
US $333/Night
7 Nights - US $2,331
US $1,105/Night
7 Nights - US $7,733
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
544 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $317/Night
7 Nights - US $2,220
House
3 Bedrooms
2 Baths
6 Guests
3003.13 ft²
- Balcony/Terrace
- View
- Parking
- Internet
US $321/Night
7 Nights - US $2,247
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $336/Night
7 Nights - US $2,353
House
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
Air Conditioner- Internet
Child Friendly
US $98/Night
7 Nights - US $686
Cabin
9.6(248 Reviews)
2 Bedrooms
1 Bath
4 Guests
640 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $267/Night
7 Nights - US $1,869
Chester Luxury Rentals
New
House
4 Bedrooms
4 Baths
9 Guests
3304.52 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Parking
US $988/Night
7 Nights - US $6,918
House
4.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
1750 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $871/Night
7 Nights - US $6,099
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
3300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $760/Night
7 Nights - US $5,322
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
7 Guests
1530 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $617/Night
7 Nights - US $4,318
House
10.0(19 Reviews)
3 Bedrooms
2 Baths
10 Guests
2000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $587/Night
7 Nights - US $4,112
New
Cottage
3 Bedrooms
1 Bath
6 Guests
936 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $573/Night
7 Nights - US $4,011
Cabin
4 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Internet
- Child Friendly
Laundry
US $559/Night
7 Nights - US $3,910
House
10.0(1 Review)
4 Bedrooms
2 Baths
12 Guests
2902 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $554/Night
7 Nights - US $3,880
Chester Pet Friendly Vacation Rentals
House
9.6(23 Reviews)
3 Bedrooms
2 Baths
6 Guests
3055 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $383/Night
7 Nights - US $2,683
House
3 Bedrooms
2 Baths
6 Guests
3056.95 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $263/Night
7 Nights - US $1,841
Cabin
9.6(63 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $365/Night
7 Nights - US $2,553
Cottage
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $218/Night
7 Nights - US $1,529
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
2100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $382/Night
7 Nights - US $2,672
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
2000 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $160/Night
7 Nights - US $1,117
House
9.6(237 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $307/Night
7 Nights - US $2,150
House
10.0(102 Reviews)
4 Bedrooms
3 Baths
8 Guests
3400 ft²
Oceanfront
Hot Tub- Fireplace/Heating
- Ocean View
US $391/Night
7 Nights - US $2,737
Chester Large Vacation Homes
House
6 Bedrooms
6 Baths
16 Guests
4226 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $843/Night
7 Nights - US $5,898
New
House
4 Bedrooms
2 Baths
12 Guests
2906.26 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $509/Night
7 Nights - US $3,563
House
5 Bedrooms
3 Baths
11 Guests
2090 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $390/Night
7 Nights - US $2,730
House
9.6(25 Reviews)
4 Bedrooms
2 Baths
10 Guests
3644 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $406/Night
7 Nights - US $2,842
House
5.0(73 Reviews)
6 Bedrooms
3 Baths
10 Guests
2500 ft²
- Ocean View
- View
- Pet Friendly
- Kitchen
US $395/Night
7 Nights - US $2,765
Why Choose Rent By Owner for your Chester Vacation Rental Homes?
What makes our Vacation Rentals 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.
Best Times to Visit Chester
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here ensures you experience the region’s charm at its best, whether you're seeking quiet serenity or lively seasonal activities in Chester, Massachusetts.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warmer temperatures and longer daylight hours, making it ideal for outdoor activities and exploring the scenic region.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
Fall (September to November)
Autumn brings vibrant foliage and mild weather, providing a picturesque backdrop for your stay in this charming destination.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 55°F
Off-Season Highlights
Winter (December to February)
The winter season offers a quieter atmosphere with cooler temperatures, perfect for cozy getaways and enjoying indoor comforts.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Spring (March to May)
Early spring features milder weather and blooming landscapes, ideal for visitors seeking fewer crowds and peaceful surroundings.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Chester
How to Book Your Chester Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals 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
Outdoor Amenities
- Enjoy a private outdoor space with a spacious backyard perfect for picnics and family gatherings.
- Relax by a charming fire pit area ideal for evening conversations under the stars.
- Take advantage of well-maintained outdoor seating areas to unwind and enjoy the fresh air.
- Make use of a convenient grilling station for outdoor barbecues during your stay.
- Discover scenic walking paths or trails nearby, perfect for outdoor exploration.
- Benefit from access to a swimming pool or hot tub, if available, to enhance relaxation.
- Experience outdoor recreational amenities like croquet or bocce ball for added fun in the region.
Top Attractions Around Chester
What attractions are nearby?
While staying here, you can explore nearby outdoor activities and cultural attractions that showcase the charm of the region, offering a variety of memorable experiences just moments from your vacation rental in Chester, Massachusetts.
Family Activities
- Chester Common: Spend quality time exploring this charming local park, perfect for family picnics and outdoor games amid scenic surroundings.
- Hiking at Mount Greylock State Reservation: Embark on family-friendly trails that offer breathtaking views of the region's natural beauty from the highest peak in Massachusetts.
- Discovering Local Art at Chester Gallery: Engage with the area's vibrant arts scene by visiting this gallery, showcasing works from talented regional artists suitable for all ages.
- Fishing and Relaxing at Lake Mansfield: Enjoy a peaceful day by the water, where you can fish or simply unwind while taking in the tranquil scenery of this popular local lake.
Adult Activities
- Exploring the Chester Rail Trail: Enjoy a peaceful walk or bike ride along the scenic Chester Rail Trail, offering beautiful views of the surrounding region.
- Visiting the Chester Gallery: Discover local art and craftsmanship at the Chester Gallery, perfect for immersing yourself in the area's creative culture.
- Wine Tasting at Nearby Vineyards: Indulge in wine tasting experiences at nearby vineyards, highlighting the region’s celebrated viticulture.
- Relaxing at Local Waterfront Spots: Spend leisure time at nearby waterfront locations, where you can unwind and enjoy the tranquil scenery that characterizes the area.
Other Places to Stay in Chester, MA
Chester Town Hall
Chester Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining and Markets: Take advantage of the region’s farm-to-table restaurants and local markets to enjoy authentic flavors during your stay.
- Visit Scenic Outdoor Spots: Make the most of the area's natural beauty by exploring nearby parks, trails, or waterfront areas for hiking and relaxation.
- Plan Cultural Experiences: Check out any local events, galleries, or historical sites to deepen your connection with this charming destination.
- Utilize Convenient Transportation: Arrange for transportation options or bike rentals to easily access key attractions around the area and enjoy a stress-free visit.
Transportation Options
- Chester, Massachusetts Public Transportation: You can rely on local bus services to connect you with nearby towns and attractions within the region.
- Car Rentals in Chester: Renting a car here offers flexibility to explore scenic areas and picturesque sites around this charming destination.
- Private Taxis and Rideshare Services: Convenient for quick travel to dining, shopping, or outdoor activities within this part of Massachusetts.
- Bicycle Rentals: Enjoy an eco-friendly way to discover the area's natural beauty and peaceful surroundings at your own pace.
Local Customs Options
- Traditional Seafood Dining: Many local eateries in the region uphold the maritime culinary traditions, offering fresh seafood that celebrates the area's rich fishing heritage.
- Seasonal Festivals: Participating in seasonal festivals and community events is a cherished custom, providing an authentic experience of the area's vibrant local culture.
- Historical Preservation: Respect for historical landmarks and architecture is deeply ingrained, with residents often engaging in activities to preserve the area's colonial and maritime history.
- Outdoor Recreation Etiquette: When enjoying the natural scenery here, it’s customary to follow specific outdoor etiquette, such as respecting private property and maintaining cleanliness in parks and waterfronts.
Frequently Asked Questions About Chester?
1. What are the top vacation rentals 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 Vacation Rentals in Chester:
- Lakefront Cottage In The Berkshires In Western Massachusetts
- Berkshires Lakefront Retreat
- 1840's Ship Captain's Farm Estate, 6-10 guests
- Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
- Lakefront Jewel By: Evergreen Home
- Berkshires Lakefront Gem. Cozy home w/hiking, swimming & all things cultural!
- Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts
- Lakes & Leisure: Spacious Berkshire Getaway
- Private Lake Cottage on 3 acres w/350 sq. ft. deck
- Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
2. 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:
3. How many Rentbyowner vacation rentals are available in Chester?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 52 in the Chester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chester.
4. What is the cancellation policy for vacation rentals here?
Each property in Chester, Massachusetts, has its own cancellation policy. To find specific details, please review the listing carefully or contact the property owner directly before completing your reservation.
5. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning, service charges, or local taxes vary by property. Be sure to read the full listing details or reach out to the owner to understand all costs involved before booking.
6. How do I confirm the availability of a vacation rental in the region?
Availability can be checked directly on the listing page. If you have specific dates in mind, it's recommended to contact the owner to verify current availability and secure your reservation.
7. What amenities are typically included in vacation rentals here?
Most rentals offer essential amenities like Wi-Fi, appliances, and linens, but features can differ. Review each property’s listing for detailed information or ask the owner about specific amenities you need.
8. Is it possible to modify or cancel my reservation once booked?
Modifications and cancellations depend on the individual property's policies. Consult the listing details or contact the owner directly to understand your options for changing or canceling your stay.
