Chester Holiday Rentals, Connecticut: Private House Rentals

A calm river with boats, wooden docks, and buildings along the shore.

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Go beyond your typical stay in Chester

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Our top choices for Chester hotels

Breakfast included

Hotel

Bed & breakfast

Reserve now, pay later

Pool

Desk, laptop workspace, blackout curtains, iron/ironing board

Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

1. Quality Inn Old Saybrook - Westbrook

Old Saybrook

John

2.641.027 ₫

3.037.181 ₫ total

includes taxes & fees

6 Sept - 7 Sept

2. Spark by Hilton Guilford

Guilford

Stacy

2.761.916 ₫

3.176.203 ₫ total

includes taxes & fees

13 Sept - 14 Sept

Premium bedding, desk, laptop workspace, iron/ironing board

3. Hyatt Place Uncasville - Casino Area

Montville

Ralph

2.639.736 ₫

3.035.697 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Standard Room, 1 Bedroom, Private Bathroom | Premium bedding, free WiFi, individually decorated

4. The Captain Stannard

Westbrook Center

Jessica

6.107.625 ₫

6.779.464 ₫ total

includes taxes & fees

26 Aug - 27 Aug

In-room safe, desk, blackout curtains, soundproofing

5. Fairfield by Marriott Inn & Suites Wallingford New Haven

Wallingford

Thierry

3.266.361 ₫

3.756.315 ₫ total

includes taxes & fees

30 Aug - 31 Aug

Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave | Desk, blackout curtains, iron/ironing board, free cots/infant beds

6. Best Western Plus New England Inn & Suites

Berlin

Taneesha

2.734.239 ₫

3.144.375 ₫ total

includes taxes & fees

19 Aug - 20 Aug

7. Inn at Middletown

Washington Street Historic District

Dale

2.597.945 ₫

3.509.837 ₫ total

includes taxes & fees

17 Aug - 18 Aug

Desk, laptop workspace, iron/ironing board, cots/infant beds

8. Springhill Suites by Marriott Hartford Cromwell

Cromwell

Erika

3.890.390 ₫

4.473.949 ₫ total

includes taxes & fees

7 Sept - 8 Sept

37-inch flat-screen TV with cable channels, TV

9. Homewood Suites by Hilton Wallingford-Meriden

Wallingford

Timothy

3.750.702 ₫

4.313.307 ₫ total

includes taxes & fees

7 Sept - 8 Sept

10. Courtyard New Haven Wallingford

Wallingford

Marjory

3.861.669 ₫

4.440.919 ₫ total

includes taxes & fees

23 Aug - 24 Aug

Room, 1 Queen Bed, Non Smoking | In-room safe, desk, laptop workspace, blackout curtains

Studio Suite, 1 Queen Bed, Accessible, Non Smoking (Mobility/Hearing Impaired) | In-room safe, desk, laptop workspace, blackout curtains

Studio Suite, 1 Queen Bed, Non Smoking | In-room safe, desk, laptop workspace, blackout curtains

11. Microtel Inn & Suites by Wyndham Uncasville Casino Area

Montville

Donald

2.130.576 ₫

2.450.162 ₫ total

includes taxes & fees

24 Aug - 25 Aug

Free cots/infant beds, rollaway beds, free WiFi, bed sheets

12. Clinton Motel

Clinton

David

2.062.690 ₫

2.372.094 ₫ total

includes taxes & fees

2 Sept - 3 Sept

Standard Room, 2 Queen Beds | Premium bedding, down duvets, pillow-top beds, in-room safe

13. Holiday Inn Express Branford-New Haven by IHG

Branford

Carolyn

3.315.970 ₫

3.813.365 ₫ total

includes taxes & fees

23 Aug - 24 Aug

Luxury Room, 1 Bedroom, Non Smoking (Room 314) | Blackout curtains, iron/ironing board, free WiFi, bed sheets

14. Copper Beech Inn

Ivoryton

Gregg

7.284.690 ₫

8.377.394 ₫ total

includes taxes & fees

23 Aug - 24 Aug

15. Comfort Inn & Suites Meriden East

Meriden

Sharmarie

2.345.984 ₫

2.697.882 ₫ total

includes taxes & fees

2 Sept - 3 Sept

Desk, iron/ironing board, free WiFi, bed sheets

16. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Egor

2.666.353 ₫

3.066.358 ₫ total

includes taxes & fees

23 Aug - 24 Aug

3 restaurants; breakfast, lunch, dinner and brunch served

17. Water's Edge Resort & Spa

Westbrook Center

Thomas

6.563.721 ₫

7.998.677 ₫ total

includes taxes & fees

1 Sept - 2 Sept

18. Hampton Inn & Suites Rocky Hill - Hartford South

Rocky Hill

Fitzroy

3.190.120 ₫

3.668.638 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Cabin, 1 Queen Bed | Private kitchen | Mini-fridge, stovetop, cookware/dishes/utensils, paper towels

19. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

East Haddam

Frank

3.528.766 ₫

6.460.201 ₫ total

includes taxes & fees

17 Aug - 18 Aug

Suite, 1 King Bed | Living area | 42-inch LCD TV with satellite channels, TV

20. Hilton Garden Inn Wallingford/Meriden

Wallingford

Brian

3.618.324 ₫

4.161.073 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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Where to stay in Chester

Find the best Chester areas for the activities you enjoy most.Learn more about Chester

Chester Center

A plate of food with three square pieces topped with greens and caviar.

A cocktail in a martini glass on a bar counter.

Chester Center

If you're spending some time in Chester Center, Norma Terris Theater and Connecticut Valley Railroad State Park Trail are top sights worth seeing.

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Stay near popular Chester attractions

Norma Terris Theater

The Norma Terris Theatre is Goodspeed Musicals' developmental space where innovative productions debut. In this intimate setting, audiences witness tomorrow's Broadway hits evolve before their eyes.

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Learn more about Chester

Charming galleries and local shops line Main Street, where you'll find handcrafted jewellery and Connecticut River Valley artwork. Catch a performance at the Goodspeed Opera House in East Haddam or kayak Chester Creek when summer temperatures rise.

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A historic waterfront estate with a large white building featuring a balcony and a flagpole.

Top Chester Hotel Reviews

Motel 6 New Haven - Branford, CT

10/10 Excellent

"Excellent service great staff"

Hyatt Place Uncasville - Casino Area

8/10 Good

"Need to be aware of problems that come with the aging of the place… some renovations needed"

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Great location & convenient to everything. Shawn (I believe his name was) was so helpful & friendly! Older place but was good for 1 night."

Water's Edge Resort & Spa

10/10 Excellent

"Great staff Multiple food and drink options"

The Spa at Norwich Inn

10/10 Excellent

"Was a welcome surprise! Did not realize they had a spa available to guess which was nice. Enjoyed our dinner at their restaurant."

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

10/10 Excellent

"Afternoon staff woman was not nice at all morning staff man excellent"

Regency Inn & Suites New London, Mystic

10/10 Excellent

"The place was clean, smelled, nice.The staff were very helpful, always offering suggestions and kind and polite. The curry is excellent. The breakfast buffet was good."

Days Inn by Wyndham Berlin Meriden

10/10 Excellent

"Good"

Best Western Plus New England Inn & Suites

10/10 Excellent

"Great breakfast."