Chester Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chester vacation homes
#24 *Serenity* A Lakefront Cottage Retreat
#24 *Serenity* A Lakefront Cottage RetreatMiddletown
9.8 out of 10, Exceptional, (23 reviews)
"It was great "
Rodrigo C.
The price is CA $258
CA $535 total
includes taxes & fees
Jul 22 - Jul 23
Rogers Lake House (87) · CT College+Beach+USCGA
Rogers Lake House (87) · CT College+Beach+USCGAOld Lyme
10.0 out of 10, Exceptional, (9 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
Cheryl H.
The price is CA $223
CA $696 total
includes taxes & fees
Jul 20 - Jul 21
Newly Remodeled 1-BR Close to Everything yet Very Private
Newly Remodeled 1-BR Close to Everything yet Very PrivateWallingford
10.0 out of 10, Exceptional, (10 reviews)
"Best stay ever! Parking lot was easy; apartment was clean and felt like home. Bed comfortable. Would booked this apartment next trip. My only recommendation that was the kitchen did not have a toaster. "
Linda v.
The price is CA $165
CA $413 total
includes taxes & fees
Jul 19 - Jul 20
Adorable Cottage, 5 min walk to water & town
Adorable Cottage, 5 min walk to water & townWestbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
Donovan V.
The price is CA $249
CA $594 total
includes taxes & fees
Jul 20 - Jul 21
Cozy, comfy,quiet &close to casinos
Cozy, comfy,quiet &close to casinosMontville
9.4 out of 10, Exceptional, (58 reviews)
"It was great ocation for a weekend get away with friends to Mohegan Sun"
Teresa M.
The price is CA $186
CA $421 total
includes taxes & fees
Jul 21 - Jul 22
The Beach Nest-Lux Cottage Steps to the Beach
The Beach Nest-Lux Cottage Steps to the BeachClinton
9.8 out of 10, Exceptional, (6 reviews)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
Karol W.
The price is CA $348
CA $827 total
includes taxes & fees
Jul 19 - Jul 20
Once the old Schools house now a newly furnished Apartment
Once the old Schools house now a newly furnished ApartmentWallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
Jeanette W.
The price is CA $165
CA $413 total
includes taxes & fees
Aug 7 - Aug 8
Peek-A-Boo View, Amston Lake
Peek-A-Boo View, Amston LakeLebanon
9.8 out of 10, Exceptional, (52 reviews)
"Everything was perfect! "
Melissa R.
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.
Find vacation rentals that suit your style
Villas
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Chester Hotel Reviews
Best Western Niantic - New London/Mystic Area
10/10 Excellent
Find out more about Chester
Chester Vacation Homes information
Number of reviews | 9,749 |
|---|---|
Accommodation | 367 Vacation Homes |
Lowest Price | CA $123 |
Highest Price | CA $507 |
Explore a world of travel with Expedia
- Westbrook Inn B&B
- Motels in New Haven
- The Homestead
- Hotels & Resorts for Couples in Deep River Center
- Oceanfront Hotels in Madison
- Apartments in Baltic
- B&B in Manchester
- Middletown Hotels
- B&B in North Haven
- B&B in Durham
- B&B in Hartford
- Lodges in Chester
- Clinton Hotels
- New Haven Hotels
- Hawks Nest Beach Home
- Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
- B&B in Deep River
- Cabin Rentals in Rocky Hill
- Cabin Rentals in Essex
- Waterfront Cottage w/ Sunroom + Patio & Grill
- Boardman House Inn Bed & Breakfast
- B&B in Guilford
- Apartments in Mystic
- Apartments in Branford
- Guest Houses in Bethany
- Salem Hotels
- 4 Star Hotels in Durham
- Hartford Hotels
- Colchester Hotels
- Cabin Rentals in Deep River
- Beach Hotel Hotels in Old Lyme
- Durham Hotels
- Bee and Thistle Inn
- Spa Hotels in Essex
- Hotels near Brownstone Exploration & Discovery Park
- Pet-Friendly Hotels in Guilford
- Vacation Homes in Stony Creek
- Westbrook Hotels
- Hilton Hotels in Deep River
- Copper Beech Inn
- Old Saybrook Hotels
- Pet-Friendly Hotels in Middletown
- The Bevin House Bed & Breakfast
- Higganum Hotels
- La Quinta Inn & Suites Hotels in Madison
- Hostels in Hartford
- B&B in Mason's Island
- B&B in Stony Creek
- Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
- Cabin Rentals in Coastal Connecticut
- Madison Hotels
- Townhomes in Kensington
- B&B in Oakdale
- East Haddam Hotels
- Cabin Rentals in Salem
- Water's Edge Resort & Spa
- Apartments in Cobalt
- Fenwick Hotels
- Villas in Cheshire Historic District
- East Lyme Hotels
- Best Western Hotels in Deep River
- Passport Inn and Suites Middletown
- Red Roof Inn PLUS+ & Suites Guilford
- Hotels near Wesleyan University
- Essex Hotels
- Hotels near Machimoodus State Park
- Hotels near Clinton Crossing Premium Outlets
- Chester Hotels
- B&B in Bethany
- Old Lyme Hotels
- Cottages in Kensington
- Rv Parks in Hamden
- Motels in Bolton
- Motels in North Branford
- Marriott Hotels & Resorts in Essex
- Flights to Uncasville
- Flights from Toronto (YYZ) to New Haven (HVN)
- Flights from Vancouver (YVR) to New Haven (HVN)
- Flights to Chester
- Flights to Killingworth
- Flights to Middletown
- Flights to Old Saybrook
- Flights to East Hampton
- Flights to Moodus
- Flights to Madison
- Flights to Essex
- Flights to Connecticut
- Flights from Montreal (YUL) to New Haven (HVN)
- Flights to Guilford
- Flights from Toronto (YYZ) to Hartford (BDL)
- Flights to Clinton