Vacation Rentals in Chalker Beach, CT: Compare 10+ Sites & Save

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189 Best Vacation Rentals in Chalker Beach (Starting from $168)

Grandmas Cottage with Sunroom Walk to Beach
Grandmas Cottage with Sunroom Walk to Beach
House
Old Saybrook, CT, USA
0.9k from Chalker Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms5 Guests
New to Booking
$284
Average price / night
Check Availability
1910 Beach home: CT's most exquisite private beach!
1910 Beach home: CT's most exquisite private beach!
House
Old Saybrook, CT, 06475, United States
0.1k from Chalker Beach center

Barbecue, Fireplace, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio

4 Bedrooms10 Guests
9.6

Exceptional

13 reviews

$575
Average price / night
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Charming Westbrook Cottage, Steps to Private Beach
Charming Westbrook Cottage, Steps to Private Beach
House
Westbrook, CT, USA
1.1k from Chalker Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

3 Bedrooms7 Guests
6.7

Good

3 reviews

$226
Average price / night
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Chalker Beach House Steps to the Water!
Chalker Beach House Steps to the Water!
House
Old Saybrook, CT, 06475, United States
0.2k from Chalker Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
8.0

Good

2 reviews

$985
Average price / night
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Dreamy Waterfront Westbrook Home on Private Beach
Dreamy Waterfront Westbrook Home on Private Beach
House
Westbrook, CT, USA
1.1k from Chalker Beach center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Pet-friendly, Lodgings, Beach

3 Bedrooms6 Guests
New to Booking
$276
Average price / night
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Chalker Beach, Beachfront Home in Old Saybrook, Connecticut,
Chalker Beach, Beachfront Home in Old Saybrook, Connecticut,
House
Old Saybrook, CT, 06475, United States
0.4k from Chalker Beach center

AC, Dryer, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$805
Average price / night
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Saybrook Manor Beach House
Saybrook Manor Beach House
House
Old Saybrook, CT, USA
1.1k from Chalker Beach center

Child Friendly, Laundry, View, Private Beach, Internet, Air Conditioner, Balcony/Terrace

3 Bedrooms10 Guests
8.0

Good

1 reviews

$285
Average price / night
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Charming year-round beach home in Indian Town, Old Saybrook
Charming year-round beach home in Indian Town, Old Saybrook
House
Old Saybrook, CT, 06475, United States
0.6k from Chalker Beach center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.6

Exceptional

7 reviews

$703
Average price / night
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Great Hammock Getaway
Great Hammock Getaway
House
Old Saybrook, CT, USA
1.3k from Chalker Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Jacuzzis

3 Bedrooms8 Guests
9.8

Exceptional

5 reviews

$301
Average price / night
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Charming waterfront cottage in Indiantown Old Saybrook
Charming waterfront cottage in Indiantown Old Saybrook
Cottage
Old Saybrook, CT, 06475, United States
0.6k from Chalker Beach center

Barbecue, Fireplace, Free Parking, Heater, Living Area, Microwave, No Smoking, TV

1 Bedroom3 Guests
New to Booking
$335
Average price / night
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Cozy apartment, private beach & jacuzzi
Cozy apartment, private beach & jacuzzi
Apartment
Westbrook, CT, USA
1.3k from Chalker Beach center

Apartments, Cheap, Accommodations, Parking, Lodgings, Beach, Jacuzzis, Places to stay, Self-catering

1 Bedroom4 Guests
9.5

Superb

8 reviews

$168
Average price / night
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Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12  Linens Included
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
House
Old Saybrook, CT, 06475, United States
0.6k from Chalker Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms12 Guests
10.0

Exceptional

35 reviews

$819
Average price / night
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Westbrook Home with Ocean Views - Walk to Beach
Westbrook Home with Ocean Views - Walk to Beach
House
Westbrook, CT, USA
3.2k from Chalker Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
3.0

Review score

1 reviews

$339
Average price / night
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Beach House steps to private beaches in sought after location!
Beach House steps to private beaches in sought after location!
House
Old Saybrook, CT, 06475, United States
0.6k from Chalker Beach center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

46 reviews

$561
Average price / night
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Charming Old Saybrook Cottage Less Than 1 Mi to Beach
Charming Old Saybrook Cottage Less Than 1 Mi to Beach
House
Old Saybrook, CT, USA
3.5k from Chalker Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$474
Average price / night
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Chalker Beach cottage, steps to private beach.
Chalker Beach cottage, steps to private beach.
Cottage
Old Saybrook, CT, 06475, United States
0.7k from Chalker Beach center

AC, Heater, No Smoking

3 Bedrooms6 Guests
New to Booking
$529
Average price / night
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Cozy Westbrook Vacation Rental - Walk to Beach!
Cozy Westbrook Vacation Rental - Walk to Beach!
House
Westbrook, CT, USA
4.6k from Chalker Beach center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.0

Fabulous

3 reviews

$460
Average price / night
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Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach
Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach
Cottage
Old Saybrook, CT, 06475, United States
0.7k from Chalker Beach center

AC, Barbecue, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
10.0

Exceptional

38 reviews

$258
Average price / night
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The Sharlene Cottage
The Sharlene Cottage
House
Chalker Beach, Old Saybrook, Connecticut, USA
7.8k from Chalker Beach center

Internet, View, Kitchen, Air Conditioner, Parking, Oceanfront, Smoking

3 Bedrooms8 Guests
New to Booking
$450
Average price / night
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Family Friendly, Beach Themed Cottage - Chalker Beach
Family Friendly, Beach Themed Cottage - Chalker Beach
Cottage
Old Saybrook, CT, 06475, United States
0.7k from Chalker Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

60 reviews

$299
Average price / night
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Waterfront Cottage with Sunroom and Patio and Grill
Waterfront Cottage with Sunroom and Patio and Grill
House
Clinton, CT, USA
9.4k from Chalker Beach center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$233
Average price / night
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Waterfront home in the town of Old Saybrook, CT, walk to beach in a minute.
Waterfront home in the town of Old Saybrook, CT, walk to beach in a minute.
House
Old Saybrook, CT, 06475, United States
0.8k from Chalker Beach center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$1283
Average price / night
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54 Steps to the Beach
54 Steps to the Beach
House
Old Saybrook, CT, 06475, United States
0.8k from Chalker Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.6

Exceptional

8 reviews

$517
Average price / night
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Great family home, fenced in back yard and Weber grill.
Great family home, fenced in back yard and Weber grill.
House
Old Saybrook, CT, 06475, United States
0.8k from Chalker Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

40 reviews

$471
Average price / night
Check Availability
Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Cottage
Old Saybrook, CT, 06475, United States
0.9k from Chalker Beach center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms5 Guests
9.8

Exceptional

9 reviews

$391
Average price / night
Check Availability
RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.
RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.
Cottage
Westbrook, CT, 06498, United States
0.9k from Chalker Beach center

AC, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

4 Bedrooms8 Guests
9.8

Exceptional

113 reviews

$357
Average price / night
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Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
House
Old Saybrook, CT, 06475, United States
0.9k from Chalker Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

50 reviews

$205
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Chalker Beach.

Where to stay in Chalker Beach? Best neighborhoods & areas

Chalker Beach Vacation Rentals on the Map

Frequently Asked Questions

You can explore 189 verified vacation rentals in Chalker Beach. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Chalker Beach vary depending on the season, property size, and location. Rates typically start from around $168 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Chalker Beach include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Chalker Beach welcome pets. Currently, 18 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Chalker Beach often include amenities such as View, Internet, and Ocean View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.