Chester holiday rentals

We found 332 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:6 Nov - 13 Nov

Room
Exterior
Dining
Interior
Exceptional
(67 reviews)

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

Westbrook

8% off
AU$9,986
for 7 nights, 1 home
AU$1,427 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Exterior
Interior
Living area
Private kitchen
Exceptional
(30 reviews)

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Durham

8% off
AU$7,501
for 7 nights, 1 home
AU$1,072 per night
includes taxes & fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Interior
Living area
Dining
Private kitchen
Exceptional
(11 reviews)

Sunny, Beach Days - Enjoy the beach just steps away in Clinton, Connecticut

Clinton

8% off
AU$7,866
for 7 nights, 1 home
AU$1,124 per night
includes taxes & fees
Sunny, Beach Days - Enjoy the beach just steps away in Clinton, Connecticut
Outdoor dining
Inner Hall
Entry Hall
Whitefield Rock and rear view of Ludington House (Whitefield Suite is at left)
Exceptional
(20 reviews)

Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques

Old Lyme

10% off
AU$21,194
for 7 nights, 1 home
AU$3,028 per night
includes taxes & fees
Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques
Dining
Living area
Interior
Front of Historic Mansion B&B
Exceptional
(5 reviews)

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

Higganum

8% off
AU$2,545
for 7 nights, 1 room
AU$364 per night
includes taxes & fees
Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance
Living area
Living area
Room
Interior
Exceptional
(19 reviews)

Room for the whole family 1/2 hour to Mohegan and Mystic Seaport

Colchester

8% off
AU$3,499
for 7 nights, 1 home
AU$500 per night
includes taxes & fees
Room for the whole family 1/2 hour to Mohegan and Mystic Seaport
Dining
Exterior
Living Room with view of expandable dining table
Deck
Exceptional
(88 reviews)

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton

7% off
AU$2,083
for 7 nights, 1 cottage
AU$298 per night
includes taxes & fees
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
3 season porch with couch, 2 upholstered chairs and coffee table
Property grounds
Private kitchen
Level 2 (240V/40amp) EV charger available
Exceptional
(11 reviews)

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

Higganum

16% off
AU$4,686
for 7 nights, 1 home
AU$669 per night
includes taxes & fees
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Interior
Interior
Exterior detail
Exterior detail
Exceptional
(139 reviews)

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Old Saybrook

8% off
AU$5,260
for 7 nights, 1 home
AU$751 per night
includes taxes & fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Living Room
Saybrook Point Cottage
local marinas
South Cove at the end of the street
Exceptional
(143 reviews)

Saybrook Point Cottage - Charming and Private

Old Saybrook

15% off
AU$2,179
for 7 nights, 1 cottage
AU$311 per night
includes taxes & fees
Saybrook Point Cottage - Charming and Private
Private kitchen
Property grounds
Private kitchen
Room
Exceptional
(63 reviews)

Summer at the Haddam House

Haddam

8% off
AU$2,593
for 7 nights, 1 home
AU$370 per night
includes taxes & fees
Summer at the Haddam House
Kitchen
Pathway leading to Birdsong- spring
Kitchen and living room
Livingroom and Kitchen
Exceptional
(92 reviews)

Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town

Madison

12% off
AU$2,042
for 7 nights, 1 apartment
AU$292 per night
includes taxes & fees
Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town
Living area
Dining
Private kitchen
Cute town at night - Little House Brewery
Exceptional
(25 reviews)

The Millhouse Downtown Chester

Chester

8% off
AU$3,728
for 7 nights, 1 apartment
AU$533 per night
includes taxes & fees
The Millhouse Downtown Chester
Gateway to tranquility at the private beach is only a 5 minute walk.
Enter into the open floor plan with updated kitchen, living, and family room.
Covered patio is well lit with overhead lighting.
Seat 6 people at the dining table, or use it to get some work done.
Exceptional
(78 reviews)

UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

Westbrook

8% off
AU$4,681
for 7 nights, 1 home
AU$669 per night
includes taxes & fees
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

  • 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:

  • Chatfield Hollow State Park (6.2 mi / 9.9 km)
  • 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)
  • The Book Barn (15.3 mi / 24.6 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:

  • Chatfield Hollow State Park (6.2 mi / 9.9 km)
  • Bashan Lake (7.1 mi / 11.4 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)
  • 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 home?
One of the more popular neighbourhoods to get a holiday home in Chester is Chester Centre. Discover a dream stay with Stayz and explore this area like a local.
What is the most popular type of holiday home accommodation in Chester?
The most desirable types of holiday homes in Chester are apartments. Ready for more choices? Stayz has many options to match the unique needs of our guests, so you'll see holiday properties in all shapes and sizes. The ideal home away from home is waiting for you — book yours today.
How much does it cost to rent a holiday home in Chester?
Different things affect what you'll pay for your holiday home in Chester, such as the type of property, length of stay and season. But, all our holiday homes have something in common — amazing value. Just add your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Chester?
When you travel and the style and size of the property will influence how much you'll pay for your beachside holiday home. Click on your Chester travel dates to view your available options on Stayz. Did someone just say "hot tub"? Use the filters to pick the features and amenities you want in your holiday home.
Are there pet-friendly holiday homes in Chester?
Pack up a suitcase for your pooch because Chester has two holiday homes that open their doors to pets. Let your happy hound have fun with the family at one of our pet-friendly holiday homes on Stayz. Simply enter your destination and travel dates, then check the "Pets allowed" filter box.
What are popular home amenities in Chester?
When it comes to home amenities that guests look for in Chester, a nearby waterfront, a barbecue grill and nearby museums are the most popular. With Stayz holiday homes, you'll discover options to match your taste and style, whether you're taking a trip with your partner, your family or even pets.
Are there large group holiday homes in Chester?
Take your pick of two Stayz properties in Chester that can accommodate a group of five or more people. You'll get all the space and privacy you need to hang out with your favourite people — and nobody else.
Are there holiday homes in Chester that welcome kids?
With two family-friendly holiday homes to choose from in Chester, now is a great time to introduce your children to the joys of travel. Just check our "Properties good for families" filter to browse stays packed with conveniences perfect for travelling families, like living rooms, yards, bunk beds and entertainment areas.
What are the top attractions for families in Chester?
Keeping the kids happy during your holiday in Chester is easy with these family-friendly attractions:
  • Essex Steam Train
  • Connecticut River Museum
  • Stay and Play LLC
How old do you have to be to rent a holiday home in Chester?
It's advisable to check with the Chester holiday home you're considering on Stayz as the age limit differs. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Chester for?
It's up to the Chester property. To see all available options offering extended stays, simply type your dates and number of guests into the Stayz search page. Look forward to having the entire place to yourself, along with home comforts like air conditioning, a fully-equipped kitchen and outdoor spaces where the little ones can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.