Chester holiday homes

We found 328 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Chester that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Chester

Showing deals for:18 Dec - 25 Dec

Basement - Full Kitchen, Pull out couch
Outdoor patio fireplace, patio heaters.
Private kitchen
Pool
Exceptional
(57 reviews)

Resort style getaway w/pool, spa, game room & more

East Haddam

7% off
NZ$14,384
for 7 nights, 1 home
NZ$2,055 per night
includes taxes & fees
Resort style getaway w/pool, spa, game room & more
Room
Exterior
Interior
Dining
Exceptional
(68 reviews)

Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

Westbrook

8% off
NZ$12,547
for 7 nights, 1 home
NZ$1,792 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Private kitchen
Terrace/patio
Room
Living area
Exceptional
(33 reviews)

Updated cottage "Beriozka" on Cedar Lake

Chester

7% off
NZ$2,803
for 7 nights, 1 cottage
NZ$400 per night
includes taxes & fees
Updated cottage "Beriozka" on Cedar Lake
Entryway 🐳
Property grounds
Kitchen
Dining
Exceptional
(17 reviews)

Cornfield Point Cottage

Old Saybrook

8% off
NZ$14,426
for 7 nights, 1 home
NZ$2,061 per night
includes taxes & fees
Cornfield Point Cottage
Bedroom with 2 single Beds
Living area
Interior
Front of Historic Mansion B&B
Exceptional
(6 reviews)

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance

Higganum

8% off
NZ$3,065
for 7 nights, 1 room
NZ$438 per night
includes taxes & fees
Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance
3 season porch with couch, 2 upholstered chairs and coffee table
Property grounds
Private kitchen
Level 2 (240V/40amp) EV charger available
Exceptional
(13 reviews)

Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

Higganum

16% off
NZ$5,784
for 7 nights, 1 home
NZ$826 per night
includes taxes & fees
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Room
Beach
Living area
Private kitchen
Exceptional
(32 reviews)

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

Clinton

11% off
NZ$6,784
for 7 nights, 1 home
NZ$969 per night
includes taxes & fees
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
One full bedroom w two full sleeper sofas to accommodate 4 guests comfortably.
Property grounds
Private kitchen
Private kitchen
Exceptional
(67 reviews)

Summer at the Haddam House

Haddam

8% off
NZ$3,123
for 7 nights, 1 home
NZ$446 per night
includes taxes & fees
Summer at the Haddam House
Living area
Dining
Exterior
Room
Exceptional
(47 reviews)

Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

Westbrook

6% off
NZ$5,584
for 7 nights, 1 home
NZ$798 per night
includes taxes & fees
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Theatrical Chester will entice you

Enjoy the theatre scene and other features of Chester. One of the city's many top draws is its parks. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Chester

Are you looking for attractions to see while you're in town? Venture out of your cosy holiday rental and experience everything that Chester has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Machimoodus State Park (6.5 mi / 10.5 km)
  • Dinosaur Place at Nature's Art (13.7 mi / 22 km)
  • Brownstone Exploration & Discovery Park (14.6 mi / 23.5 km)
  • Powder Ridge Mountain Park and Resort (15 mi / 24.2 km)
  • TPC River Highlands (17.8 mi / 28.7 km)
  • Chatfield Hollow State Park (6.2 mi / 9.9 km)

Exploring the natural features in Chester

Whether you're an active traveller or just want to appreciate the scenery, Chester is a great spot to appreciate mother nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Crystal Lake Town Park (8 mi / 12.8 km)
  • Goose Island (8.3 mi / 13.3 km)
  • Westbrook Town Beach (8.7 mi / 14 km)
  • Clinton Town Beach (9.4 mi / 15.2 km)
  • Chalker Beach (9.5 mi / 15.3 km)
  • Harvey's Beach (10 mi / 16 km)

Travelling to and around Chester

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 23.1 mi (37.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into New London, CT (GON-Groton - New London), which is 23.1 mi (37.2 km) away.

Frequently asked questions

What is the best area to stay in Chester when booking a holiday rental?
When considering a holiday rental in Chester, Connecticut, the picturesque neighbourhood of Chester Village is an excellent choice. This charming area offers a delightful blend of quaint shops, art galleries, and restaurants, making it vibrant and inviting for visitors. A must-see in Chester Village is the historic Chester Meeting House, which showcases beautiful architecture and serves as a focal point for community events. Additionally, the nearby Connecticut River provides opportunities for kayaking and scenic strolls along the waterfront.Another appealing option is the neighbourhood surrounding the scenic Pattaconk Lake. This area is particularly great for nature enthusiasts, as it features lovely hiking trails and picturesque views. The tranquillity of the lake makes it great for picnics or simply relaxing in a serene environment.Overall, Chester boasts a selection of properties that cater to various preferences, providing visitors with a comfortable base to explore this charming town and its attractions.
What is the most popular type of holiday rental accomodation in Chester?
In Chester, holiday houses are the most popular type of holiday rental, with several available throughout the charming town. These properties often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many include outdoor spaces such as patios or gardens, great for enjoying the scenic surroundings. Additionally, there are several cottages and apartments available, which provide a cozier atmosphere and typically come with essential amenities like kitchen facilities and comfortable living areas.
Are there any family house rentals in Chester?
In Chester, Connecticut, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This charming town features a variety of properties, many of which are situated close to local parks and recreational areas. Visitors can expect spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor spaces great for kids to play in.Nearby attractions include the picturesque Chester Village, where families can enjoy boutique shopping and delightful dining options. Additionally, the area is not far from the scenic Connecticut River, offering opportunities for outdoor activities such as kayaking and hiking.
Are there pet-friendly house rentals in Chester?
In Chester, Connecticut, there are several pet-friendly house rentals available, making it a great destination for travellers looking to bring their furry companions along. Many of these holiday homes come equipped with amenities such as spacious kitchens, outdoor decks or patios, and comfortable living areas, ideal for families or groups. The scenic charm of Chester is complemented by proximity to various parks and nature spots, allowing for enjoyable walks and outdoor activities with pets. Local attractions, including the picturesque Chester Village, offer delightful shops and eateries that welcome pets, enhancing the overall experience for visitors.
Are there any remote work holiday rentals in Chester?
In Chester, Connecticut, there are numerous remote work holiday rentals available, with around 15 options for those looking to combine work and leisure. The charming town is known for its quaint New England atmosphere, offering a variety of properties that provide essential amenities for remote workers. Many rentals come equipped with dedicated workspaces, such as desks and ergonomic chairs, as well as reliable Wi-Fi to ensure you can stay connected during your stay.The area itself boasts picturesque views and a peaceful environment, ideal for focusing on work while also enjoying the tranquillity of the surroundings. Chester's vibrant downtown features local shops, cafes, and restaurants, providing convenient spots to unwind after a day of remote work. Additionally, the scenic Connecticut River and nearby parks offer opportunities for relaxation and outdoor activities, making this town an attractive choice for those seeking a work-friendly getaway. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Chester?
In Chester, popular holiday rental amenities include kitchens, which allow guests to prepare their own meals, and decks or patios that provide outdoor spaces for relaxation and enjoying the surrounding scenery. Many rentals also feature coffee and tea makers for that morning brew, along with fireplaces that add a cosy touch during cooler evenings. Onsite parking is commonly available, making it convenient for those travelling by car.
When is the best time to visit Chester for a holiday rental?
The peak season for holiday rentals in Chester is from May to July, with July being the most popular month for visitors. This vibrant time of year attracts families and adventure seekers looking to enjoy the charming coastal town and its many offerings. With warm temperatures averaging between 20 to 30 degrees Celsius, it's great for outdoor activities, exploring local shops, and indulging in delicious cuisine at nearby restaurants.During these summer months, you can expect a lively option filled with community events, art exhibitions, and access to beautiful parks along the Connecticut River. It's an excellent time for sightseeing, with opportunities for kayaking, hiking, and enjoying the picturesque scenery that Chester has to offer.For those looking for more budget-friendly options, consider planning your visit in January. This quieter month allows for a more relaxed experience, where you can appreciate Chester's quaint charm without the hustle and bustle of peak season. While temperatures can drop to around -5 degrees Celsius, the serene winter landscape offers a unique perspective of the town, great for peaceful walks and cozying up in local cafés.Ultimately, your best time to visit Chester for a holiday rental will depend on your preference for vibrant summer activities or tranquil winter exploration.
What are the top attractions in Chester?
In Chester, Connecticut, visitors can enjoy a charming blend of natural beauty and historic sites. The picturesque downtown area is dotted with local shops, cafes, and art galleries, providing a quaint atmosphere great for leisurely strolls. One of the town's highlights is the Chester Museum at the Mill, which offers insights into the local history and heritage.For outdoor enthusiasts, the nearby Chester Creek and the scenic landscapes of the Connecticut River Valley offer opportunities for hiking, kayaking, and enjoying nature. The town also hosts various events throughout the year, including the annual Chester Fair, which showcases local agriculture and crafts.Additionally, the beautiful Gillette Castle State Park, located a short drive away, features stunning views and hiking trails, making it a popular spot for both locals and visitors.
Are all fees included in the Chester holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chester holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Chester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chester holiday homes?
You can find great discounts on holiday homes in Chester on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chester holiday home booking on Bookabach?
To find Chester holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Chester?
A long-stay holiday home in Chester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chester holiday home?
Book your Chester holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chester?
Prices for holiday homes in Chester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Chester to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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