Name: New Haven Hotel
Price range: CA $189
Rating: 9.2

Your Cheshire Vacation

There's plenty to love about Cheshire, from its rich history to its spectacular views and beyond. When you're ready to say hello to this lively city, our Cheshire vacation packages will be just the ticket. Any trip to Cheshire needs a well-crafted itinerary. Fill yours with leading attractions like Toyota Oakdale Theatre, Choate Rosemary Hall and Mount Southington Ski Area. Expedia will help you escape your daily routine. Tailor your vacation to Cheshire to suit your style of travel, whatever that may look like.

Top Cheshire Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Hamden Hotel and Suites – Hamden New Haven

CA $1,204

per person

Aug 20 - Aug 24

found 24 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to New Haven (HVN)

6.8/10 (1,001 reviews)

Breakfast was enjoyable.

Reviewed on May 24, 2026

Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

CA $1,342

per person

Aug 20 - Aug 24

found 24 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to New Haven (HVN)

8/10 Very Good! (1,000 reviews)

Comfortable for a nights stay. Close to nice restaurants and shopping.

Reviewed on May 21, 2026

La Quinta Inn & Suites by Wyndham New Haven

Long Wharf

CA $1,234

per person

Aug 20 - Aug 24

found 24 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to New Haven (HVN)

6/10 (1,262 reviews)

The hotel staff was excellent and very reasonable and the property is essentially located

Reviewed on May 24, 2026

Beechmont - Perfect for Family Retreat!

North End

CA $3,699

per person

Aug 1 - Aug 5

found 2 hours ago

Roundtrip flight included

Halifax (YHZ) to New Haven (HVN)

No reviews

Liberty Inn

CA $1,229

per person

Aug 20 - Aug 24

found 24 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to New Haven (HVN)

7.6/10 Good! (648 reviews)

Perfect clean and safe for a quick overnight stay. Owner is very nice and polite. There are no amenities. Only complaint I have is that is if right on I-95 and is noisy.

Reviewed on May 25, 2026

Ready to book your vacation to Cheshire?

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Cheshire Hotel Deals

Cheshire Welcome Inn

1106 S Main St. Cheshire CT

Fully refundableReserve now, pay when you stay

CA $123

CA $141 total

Jun 1 - Jun 2

includes taxes & fees

8.4/10 Very Good! (817 reviews)

"The staff were great. I left my $85 flashlight behind in my room."

Reviewed on May 28, 2026

The Capitol Hotel

440 Asylum St Hartford CT

Fully refundableReserve now, pay when you stay

CA $160

CA $184 total

May 31 - Jun 1

includes taxes & fees

7.4/10 Good! (1,337 reviews)

"The sink was clogged so you couldn't run the water continuously or the sink would fill and drain very slowly. The bathroom door wouldn't shut all the way, nor would it even open all the way. While the sheets on the bed were clean, the floor and carpet around the bed and furniture in the room was ..."

Reviewed on May 29, 2026

New Haven Hotel

229 George Street New Haven CT

Fully refundableReserve now, pay when you stay

CA $189

CA $217 total

Jun 7 - Jun 8

includes taxes & fees

9.2/10 Wonderful! (2,143 reviews)

"Love this hotel. I stay in it everytime I go to New Haven. The rooms are great, the staff is friendly and super helpful. It's close to things in the city. Highly recommend."

Reviewed on May 29, 2026

See all 1,278 properties in Cheshire

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.