2025 Cheshire, Connecticut Hotels

Up To 10% Off Select Hotels With AARP Member Discounts

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Choose from AARP Discount Cheshire Hotels with Free Cancellation

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
64 Knotter Dr, Cheshire, CT
Free Cancellation
5.95 km from city center
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Stay at this 3-star business-friendly hotel in Cheshire. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
3.76 km from city center
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Stay at this motel in Cheshire. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Free Cancellation
Reserve now, pay when you stay
34.6 km from city center
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Stay at this 3-star business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
22.71 km from city center
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Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
12.9 km from city center
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Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
400 Sargent Dr, New Haven, CT
23.79 km from city center
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Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St, Branford, CT
26.09 km from city center
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Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Free Cancellation
Reserve now, pay when you stay
27.03 km from city center
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Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St, Waterbury, CT
Free Cancellation
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11.92 km from city center
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Stay at this hotel in Waterbury. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
22.54 km from city center
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Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
22.54 km from city center
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Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Free Cancellation
14.13 km from city center
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Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy, Wethersfield, CT
Free Cancellation
28.89 km from city center
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Stay at this motel in Wethersfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Fairfield Inn & Suites by Marriott Plainville

Fairfield Inn & Suites by Marriott Plainville

2.5 out of 5
400 New Britain Ave, Plainville, CT
Free Cancellation
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19.25 km from city center
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Book a stay at this business-friendly hotel in Plainville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane, Milford, CT
Free Cancellation
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32.39 km from city center
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Stay at this 3-star business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

2.5 out of 5
2260 Whitney Ave, Hamden, CT
Free Cancellation
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14.3 km from city center
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Book a stay at this business-friendly hotel in Hamden. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast in our reviews. Popular ...
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Your Guide to Cheshire Hotels

AARP Travel Center Powered by Expedia® can help you get the hotel you want at a great rate, if you're visiting Cheshire for a hard-earned excursion, or you are showing your grandkids the area AARP Travel Center Powered by Expedia® can assist you in getting the exact hotel you want for a great price. We have a wide variety of hotels for you to pick between. You can take advantage of your member advantage to schedule a hotel that is near the sights you want to spend the most time at, or an elegant 5-star hotel. There is plenty to do and see in Cheshire, and as a member you can maximize your savings while you're on vacation.

Wonderful Lodgings in a Fabulous Location

There are 1,137 accommodations to pick from in Cheshire, with reviews to check out so that you can see previous guests' vacation tips and ideas for your stay in Cheshire. Cheshire is a top place to visit thanks to its rich history. Many also travel here for Cheshire's lively college area. You're sure to find an interest to do during your visit. As you begin your first steps of setting up your holiday, we can also help you set up some things to do. Thanks to our discounts, you'll be able to relax and enjoy your trip knowing you scored the best deals with us. AARP Travel Center is here to assist you.

Reserve Your Hotel with the Travel Center Today

We'll make it effortless for you to schedule your next vacation getaway. Whether you are traveling for work or leisure, we are going to make sure that you get the best prices available. So when you're ready to book your Cheshire getaway, we will help to schedule everything to make your stay stupendous. You will not have to worry about pulling out all your retirement savings to have a great time, thanks to our discounted vacations. Take advantage of our amazingly low rates because you won't be able to find anything more cost-effective then our deals. You will feel good throughout your entire vacation knowing you scored the best deal possible. Book with the Travel Center, and your wallet will be pleased that you are taking a vacation.