Chester Cottages
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Cottages in Chester
Waterfront Cottage in Branford
branford CT
Located in Branford, this cottage is by the ocean, within a 10-minute drive of Stony Creek Brewery and Polished.
Hot Tub
Kitchen
115 Rose Cottage with 2 bedroom walk to Groton Bay
Groton CT
$320 nightly
The price is $362 total per night
$362 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
With a stay at this cottage in Groton, you'll be within a 15-minute drive of Mystic Aquarium and Institute for Exploration and Mystic Seaport.
Kitchen
Washer
Historic cottage in Deep River, CT
Deep River CT
With a stay at this cottage in Deep River, you'll be within a 15-minute walk of Connecticut River and Selden Neck State Park.
Kitchen
Air conditioning
RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston.
Westbrook CT
With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Chalker Beach and Westbrook Town Beach.
Pool
Hot Tub
Direct waterfront renovated cottage.
Madison CT
With a stay at this cottage in Madison (Madison Center), you'll be within a 5-minute drive of Deacon John Grave House and Anna Mia's.
Kitchen
Washer
Guilford Carriage House at Granite Lodge!
Guilford CT
Located in Guilford, this cottage is within a 10-minute drive of Bill Miller’s Castle and Orchard Hill Plaza Shopping Center.
Pool
Kitchen
Adorable Cottage with Cottage porch, walk to water & town
Westbrook CT
With a stay at this cottage in Westbrook (Westbrook Center), you'll be within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.
Kitchen
Pet friendly
Charming 3-bedroom cottage short walk to Chalker Beach
Old Saybrook CT
With a stay at this cottage in Old Saybrook (Saybrook Manor), you'll be within a 5-minute drive of Chalker Beach and Saybrook Country Barn.
Kitchen
Washer
Luxury Tiny Home In Niantic
East Lyme CT
With a stay at this cottage in Niantic, you'll be within a 5-minute drive of Rocky Neck State Park and The Book Barn.
Kitchen
Dryer
Relax with a beautiful lake view
Colchester CT
Located in Colchester, this cottage is on the waterfront, a 1-minute drive from Lake Hayward and 8 minutes from Devil's Hopyard State Park.
Kitchen
Free WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Chester Cottages essential information
Accommodation | 133 Cottages |
|---|---|
Lowest Price | $362 |
Highest Price | $362 |
Popular accommodation | Waterfront Cottage in Branford, 115 Rose Cottage with 2 bedroom walk to Groton Bay, Historic cottage in Deep River, CT, RELAXATION!! Inviting, Cozy NE Cottage, 2 min walk to 🏖️, Midcoast NYC, Boston., Direct waterfront renovated cottage. , Guilford Carriage House at Granite Lodge!, Adorable Cottage with Cottage porch, walk to water & town, Charming 3-bedroom cottage short walk to Chalker Beach, Luxury Tiny Home In Niantic, Relax with a beautiful lake view, Charming 3-bedroom cottage in Old Saybrook with AC, WiFi, Black Point Beach Club Cottage Rental |