Top Winter Vacations - Vacation Rentals in Chalker Beach

Dates

Price

Guests

More

When do you want to travel?

We search multiple sites to find you the best prices.

Compare Price with Other Partners

From US $220

         

10.0 (66 Reviews)

Cottage

Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

• Air Conditioner
• Parking
• TV

• Connecticut
• Old Saybrook

View Availability

From US $285

         

|

8.0 (1 Review)

House

Saybrook Manor Beach House

• Air Conditioner
• Parking
• View

• Old Saybrook
• Saybrook Manor

View Availability

From US $178

         

|

9.8 (257 Reviews)

Bed & Breakfast

The Captain Stannard

• Air Conditioner
• Parking
• View

• Old Saybrook
• Westbrook Center

View Availability

From US $411

         

9.8 (48 Reviews)

House

Relaxing summer rental, walking distance to the beach, short ride to the outlets

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Westbrook Center

View Availability

From US $474

         

|

10.0 (1 Review)

House

Charming Old Saybrook Cottage Less Than 1 Mi to Beach

• Parking
• Security/Safety
• Guest Services

• Connecticut
• Old Saybrook

View Availability

From US $171

         

|

9.8 (175 Reviews)

Bed & Breakfast

Westbrook Inn B&B

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Westbrook Center

View Availability

From US $297

         

9.6 (4 Reviews)

Cottage

Now with TV - Relax in our 3-bedroom Westbrook cottage at West Beach

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Westbrook Center

View Availability

From US $168

         

|

9.5 (8 Reviews)

Apartment

Cozy apartment, private beach & jacuzzi

• Air Conditioner
• Parking
• View

• Old Saybrook
• Westbrook Center

View Availability

From US $335

         

|

9.0 (23 Reviews)

Bed & Breakfast

James Pharmacy Bed & Breakfast

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Old Saybrook Center

View Availability

From US $320

         

9.8 (111 Reviews)

Cottage

RELAXATION! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.

• Air Conditioner
• Parking
• Pool

• Old Saybrook
• Westbrook Center

View Availability

From US $434

         

10.0 (72 Reviews)

House

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

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Westbrook Center

View Availability

From US $600

         

10.0 (67 Reviews)

House

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

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Westbrook Center

View Availability

From US $462

         

10.0 (63 Reviews)

House

Spacious yard and view of Long Island Sound- walk to secluded beach!

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Westbrook Center

View Availability

From US $522

         

10.0 (46 Reviews)

House

Spacious And Luxurious Beach Home Steps From The Water

• Air Conditioner
• Parking
• TV

• Connecticut
• Old Saybrook

View Availability

From US $496

         

10.0 (46 Reviews)

House

Beach House steps to private beaches in sought after location!

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Saybrook Manor

View Availability

From US $408

         

10.0 (43 Reviews)

House

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

• Air Conditioner
• Parking
• TV

• Old Saybrook
• Westbrook Center

View Availability

From US $454

         

10.0 (37 Reviews)

House

Great family home, fenced in back yard and Weber grill.

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Saybrook Manor

View Availability

From US $328

         

10.0 (36 Reviews)

Cottage

Charming Old Saybrook Cottage < 1 Mi to Beach

• Air Conditioner
• Parking
• TV

• Connecticut
• Old Saybrook

View Availability

From US $868

         

10.0 (34 Reviews)

House

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

• Air Conditioner
• Parking
• Pet Friendly

• Connecticut
• Old Saybrook

View Availability

From US $188

         

10.0 (20 Reviews)

House

Year Round Beach house

• Air Conditioner
• Parking
• TV

• Connecticut
• Old Saybrook

View Availability

From US $1,071

         

10.0 (19 Reviews)

House

Beach front property steps from Long Island Sound!

• Air Conditioner
• Parking
• Pet Friendly

• Old Saybrook
• Westbrook Center

View Availability

From US $264

         

10.0 (13 Reviews)

House

SeaStar Beach HousenCLOSE WALK TO OCEAN Private Beach Access

• Air Conditioner
• Parking
• TV

• Connecticut
• Old Saybrook

View Availability

From US $497

         

10.0 (9 Reviews)

House

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

• Air Conditioner
• Parking
• Balcony/Terrace

• Old Saybrook
• Westbrook Center

View Availability

From US $556

         

10.0 (7 Reviews)

House

Waterfront oasis 4 bdr house in Old Saybrook direct waterfront amazing sunsets

• Air Conditioner
• Parking
• Pool

• Connecticut
• Old Saybrook

View Availability

★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chalker Beach.