Cheshire Vacation Packages

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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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
per person
Aug. 29 - Sep. 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7.8/10 Good! (795 reviews)
Overall, this was a very good experience. The room was clean, including the bed and the bathroom. Everything worked as expected, and there was plenty of hot water for showering. The TV and the WiFi worked well. It felt safe. The property is convenient to all mid-shoreline activities. It was very quiet except for one instance in which there was a family with an exuberant toddler staying in the room right above me; I notified the desk person and he took care of it right away. It's a good budget hotel choice for this area.

Reviewed on Jun. 17, 2024

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
Aug. 29 - Sep. 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.6/10 Exceptional! (8 reviews)
Near nice shops and restaurants

Reviewed on May 26, 2024

The Niantic Inn

The Niantic Inn

2 out of 5
per person
Aug. 29 - Sep. 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.4/10 Exceptional! (23 reviews)
It was a perfect relaxing weekend with my husband, and I am definitely coming back. So clean!!!

Reviewed on Jun. 10, 2024

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
Aug. 29 - Sep. 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.4/10 Exceptional! (1,004 reviews)
Enjoyed our stay. Will b back.

Reviewed on Jun. 18, 2024

Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
per person
Aug. 29 - Sep. 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7/10 Good! (807 reviews)
The area was safe and quiet and it was right off the higway. There were places to eat and shop near by The room smelled of cleaning products and the rooms were dated however we were only spending a night in a budget hotel so you get what you pay for the room had two beds and one had a stain on the sheet so we slept in the other and that one had a stain on the comforter the breakfast was continental so recommend eating someplace else. breakfast was in a brown bag and was a donut and a granola bar a fruit cup and a fruity drink if you are looking for no frills budget stay I would recommend staying here however I would check the sheets or bring your own

Reviewed on May 17, 2024

Cheshire Hotel Deals

Holiday Inn Cheshire - Southington, an IHG Hotel
Holiday Inn Cheshire - Southington, an IHG Hotel
3 out of 5
64 Knotter Dr, Cheshire, CT
Fully refundable
The price is CA $172 per night from Jun. 23 to Jun. 24
CA $172
CA $197 total
includes taxes & fees
Jun 23 - Jun 24
8.2/10 Very Good! (871 reviews)
"Nice room"

Reviewed on Jun. 16, 2024

Holiday Inn Cheshire - Southington, an IHG Hotel
Cheshire Welcome Inn
Cheshire Welcome Inn
2.5 out of 5
1106 S Main St., Cheshire, CT
The price is CA $123 per night from Jun. 26 to Jun. 27
CA $123
CA $142 total
includes taxes & fees
Jun 26 - Jun 27
8.4/10 Very Good! (564 reviews)
"The staff is wonderful and smiling. Never wanted anything. They were great!"

Reviewed on Jun. 9, 2024

Cheshire Welcome Inn
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Jul. 21 to Jul. 22
CA $204
CA $235 total
includes taxes & fees
Jul 21 - Jul 22
8.8/10 Excellent! (1,247 reviews)
"We are visiting Yale. The location of the hotel is good -- walkable to the campus and business around. The room is clean and renovated."

Reviewed on Jun. 17, 2024

New Haven Hotel
See all 1,090 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Cheshire vacation package cost?
We make it simple to travel the world, with Cheshire vacation packages starting from just CA $710. You’ll have the flexibility to combine your favorite airlines, hotels and car rental. For the ultimate getaway, why not add a couple of experiences and tours to your travel itinerary?
How do I get a cheap travel package to Cheshire?
Track down flights that suit your busy schedule, add a hotel to your booking and watch the savings grow with a Cheshire vacation package. It’s as easy as that! From flights and hotels to tours and rental cars, Expedia is your gateway to cheap travel. And with over 550 air carriers and 1,000,000 hotel options around the world to choose from, you’ll never be short of choice.
Where should I stay in Cheshire?
With so much to do in Cheshire, it makes sense to book a hotel close to its attractions. Cheshire Golf Course, Cheshire Hollow Farm and Bartlem Park are some popular ones to put on your must-see list.
What are the top hotels in Cheshire?
Whether you plan to stay for just one night or a week in Cheshire, you’ll get a good night’s sleep at Cheshire Welcome Inn. This place is a top pick for plenty of travelers.
How far in advance should I book my Cheshire vacation?
It all depends on the airline, but you can usually compare international fares on Expedia up to 12 months in advance. While it’s generally a good idea to book ahead of time, lucky travelers occasionally find a cheaper flight just weeks prior to the date of departure.
What does an Expedia Cheshire travel package include?
Hotels, flights and rental cars — we have them covered. With Expedia, you can shape your Cheshire travel package just how you like it. All you have to do is work out just what you need. Once you’ve made your booking, you can add extras like tours and activities. The more you bundle, the greater the savings!
What should I know before booking a Cheshire travel package?
When you book your hotels, flights and car rentals together, you’ll score terrific discounts. Whether you’re organizing a beach break in a villa or want to stay in a fancy hotel in the city, Expedia will make it happen for less.
Can I choose my airline with a Cheshire Expedia vacation package?
Yes — that’s one of the best things about an Expedia package. You get to decide. We have access to more than 550 airline partners all over the world, so you have lots of choice when creating your Cheshire trip.
If I'm not able to travel, can I cancel my Cheshire vacation package?
Yes, you can. We realize life happens, so we’re happy to help if you need to make changes to your Cheshire vacation package. It may be possible to cancel or amend your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Cheshire

Image for Cheshire Golf Course

Cheshire Golf Course

Enjoy a round of golf in Cheshire at Cheshire Golf Course. Experience the entertainment venues and theater scene in this romantic area.

Cheshire Golf Course
Image for Cheshire Hollow Farm

Cheshire Hollow Farm

Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theater scene in this romantic area.

Cheshire Hollow Farm
Image for Quinnipiac Recreation Area

Quinnipiac Recreation Area

Explore the great outdoors at Quinnipiac Recreation Area, a lovely green space in Cheshire. Experience the entertainment venues and theater scene in this romantic area.

Quinnipiac Recreation Area
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.