Discover Your Perfect Chester Vacation Homes

Chester Luxury Rentals

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8.3 (216 Reviews)
Hotel
Copper Beech Inn
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
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Chester Pet Friendly Vacation Rentals

10.0 (3 Reviews)
Apartment
Life on the Farm
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Chester Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Chester Vacation Rentals

Where are the best neighborhoods to stay in Chester?

When exploring Chester, Connecticut, selecting the right neighborhood to stay in can greatly enhance your visit. Whether you prefer a charming, historic district or a peaceful lakeside community, each area offers unique comforts and scenic views. By choosing a well-suited location within Chester, you can enjoy easy access to local attractions and the serene beauty of this inviting New England town. Rest assured that finding the perfect vacation rental in Chester is simple and reliable, ensuring a seamless booking experience for your memorable getaway.

Chester Center

In the heart of Chester, Connecticut, this area offers a charming setting with convenient access to local shops and eateries, making it an ideal choice for exploring the region while enjoying your stay in comfortable vacation rentals. It’s perfect for those seeking a central location that blends small-town charm with easy connectivity.

View 49+ Rentals in Chester Center

Deep River Center

Located nearby, the Deep River Center provides a tranquil atmosphere with scenic views and a peaceful ambiance, perfect for relaxing in cozy vacation rentals. Here, you can enjoy the serene surroundings while still being close to the local attractions and outdoor activities.

View 25+ Rentals in Deep River Center

Best Times to Visit Chester

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as the region offers distinct charms throughout the year, making it an ideal destination for a memorable getaway whenever you decide to book your vacation rentals.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this time, you can enjoy pleasant weather and blooming landscapes, making it ideal for exploring the area's scenic beauty and outdoor activities.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
autumn
Early Fall (September to October)

This period offers comfortable temperatures and fewer crowds, allowing you to experience the local ambiance and natural surroundings at a relaxed pace.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

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Winter (December to February)

The quieter winter months provide a peaceful retreat with potential for cozy accommodations and scenic views of the region's winter landscape.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Early Spring (March to April)

Before the peak season begins, this is a good time to visit with fewer visitors and the promise of blossoming flora in the region.

Average Temperature Daytime: 45-55°F - Nighttime: 30-40°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

More Top-Rated Vacation Rentals in Chester Area

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 outdoor seating areas perfect for relaxing and taking in the scenic views of the region.
  • Take advantage of private gardens or landscaped yards ideal for outdoor gatherings or quiet strolls.
  • Make the most of your stay with access to spacious patios or decks for dining alfresco.
  • Explore nearby walking trails or pathways that allow you to immerse yourself in the natural beauty of the area.
  • Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
  • Benefit from outdoor recreational equipment such as bicycles or kayaks available for guest use.
  • Relax by a private swimming pool or hot tub, perfect for unwinding after exploring here or nearby attractions.

Top Attractions Around Chester

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities and explore local attractions that highlight the area's natural beauty and cultural heritage, making it an ideal destination for an engaging and relaxing getaway.

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Family Activities

  • Chester Landing Park: Enjoy a day of family fun by the water with picnicking, fishing, and scenic views along the Connecticut River.
  • Goodspeed Opera House: Experience captivating live performances that can delight all ages in this historic regional theater.
  • Chester Meeting House and Historical Society: Discover local history through engaging exhibits and family-friendly educational programs in the region.
  • Chester Fairgrounds: Attend seasonal festivals and community events that provide entertainment and activities perfect for families visiting here.
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Adult Activities

  • Chester Historical Society Museum: Explore the area's rich heritage through engaging exhibits and preserved artifacts that offer a fascinating glimpse into local history.
  • Chester Main Street Shopping and Dining: Enjoy a leisurely day strolling along charming streets filled with boutique shops and cozy cafes, perfect for relaxing and indulging in regional flavors.
  • Chester Point Beach: Unwind by the water at this scenic public beach, ideal for sunbathing, swimming, or simply taking in picturesque views of the region’s coastline.
  • Chester Riverboat Tours: Embark on a guided river cruise to experience the natural beauty and tranquil waterways that define this part of Connecticut.

Other Places to Stay in Chester, CT

Chester Creek Marina
Chester Creek Marina Vacation Rentals
Chester Center
Chester Center Vacation Rentals
Norma Terris Theater
Norma Terris Theater Vacation Rentals
More Places to Stay Near Chester

Chester Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Take advantage of the region's renowned eateries to enjoy authentic cuisine and support local businesses during your stay.
  • Visit nearby natural attractions: Make the most of your trip by exploring scenic parks and outdoor spaces that showcase the area's natural beauty.
  • Plan flexible activities: Incorporate a mix of scheduled and spontaneous experiences to fully enjoy the relaxed pace and charm of this destination.
  • Communicate with your hosts: Engage with your vacation rental hosts for insider tips and personalized recommendations that enhance your visit here.

Transportation Options

  • Chester Transportation Services: Local transportation options like taxi services and shuttle buses offer convenient travel within the region, making it easy to explore nearby attractions from your vacation rental.
  • Connecticut Amtrak Station - Old Saybrook: The Amtrak station provides rail connectivity to major cities along the Northeast Corridor, ideal for day trips or arriving from afar with ease.
  • Regional Bus Services: Regional bus lines serve the area, providing an affordable and reliable means to navigate throughout Chester and the surrounding destinations.
  • Car Rental Agencies: Multiple car rental agencies operate locally, giving you the flexibility to explore the scenic region at your own pace during your stay.

Local Customs Options

  • Chester's Historic Main Street: You’ll find that locals often take pride in their well-preserved historic downtown, where traditional storefronts and architecture reflect the area's rich heritage.
  • Community Events and Festivals: Engaging in seasonal festivals and local gatherings is a common way to experience the region's welcoming spirit and strong community bonds.
  • Local Seafood Cuisine: Savoring fresh, locally caught seafood is an integral part of here’s culinary culture, reflecting the area's maritime influences.
  • Respect for Nature and Outdoors: Visitors are encouraged to appreciate and preserve the scenic beauty of the region by engaging in outdoor activities responsibly and honoring conservation efforts.

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:

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 2025 is over 59 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 in this area?

The cancellation policies vary by listing, so you should review the specific property's policy before booking. Typically, details are available on the listing page, and you may also contact the owner directly for clarification.

5. How can I find the most suitable vacation rental in Chester, Connecticut?

You can browse the listings to filter options based on your preferences, such as size, amenities, and price. Reading reviews and communicating with owners can also help ensure the property meets your expectations.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees like cleaning charges or service fees may apply, and these will be listed during the booking process. Always review the total cost before confirming your reservation.

7. Is it possible to modify or cancel my reservation if my plans change?

Reservation modification and cancellation policies depend on the individual listing. You should consult the specific property's cancellation and change policies, which are available on the listing or through direct contact with the owner.

8. What amenities are typically included in vacation rentals in this region?

Most properties offer amenities such as Wi-Fi, kitchen facilities, and parking. To ensure your needs are met, check the detailed amenities list on each listing and communicate with the owner if you have special requests.