Compare Cheshire Cottage Rentals

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Featured Cheshire Cottages

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

Kitchen

Washer

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

Kitchen

Washer

Cozy cottage with AC and lake access in charming Connecticut suburb.

This cottage features a water park and barbecue grills.

Pet friendly

Air conditioning

Direct waterfront cottage on private sandy beach

At this cottage, guests have access to barbecue grills.

Kitchen

Pet friendly

Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

Guests staying at this cottage enjoy a gym, an arcade/game room, and laundry facilities. Helpful staff is there to provide concierge services, as well as offer insight about the area. Other amenities at this family-friendly cottage include local meal delivery service, a garden, and barbecue grills.

Kitchen

Washer

Guilford Carriage House at Granite Lodge!

Guests staying at this cottage enjoy access to a marina, an outdoor pool, and free WiFi in public areas. A stay here includes free parking.

Pool

Kitchen

Cozy Home near private beach , close to New Haven area colleges Hospitals

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

Cozy 2-bedroom Cottage with Access to Bantam Lake

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

An outdoor pool and free WiFi in public areas are features at this cottage. You can take advantage of free parking if you drive.

Pool

Kitchen

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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.

Hotel Options in Cheshire

Cheshire Welcome Inn

1106 S Main St., Cheshire, CT

$80 nightly

$92 total

Nov 2 - Nov 3

Total with taxes and fees

8.4/10 Very Good! (737 reviews)

The Capitol Hotel

440 Asylum St, Hartford, CT

$103 nightly

$118 total

Oct 12 - Oct 13

Total with taxes and fees

7.4/10 Good! (1,011 reviews)

Omni New Haven Hotel at Yale

155 Temple St, New Haven, CT

$167 nightly

$192 total

Oct 26 - Oct 27

Total with taxes and fees

8.4/10 Very Good! (1,005 reviews)

Cottages

Book a cottage in Cheshire
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Cheshire. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Cheshire better.

Cottage apartments in Cheshire range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Cheshire
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Cheshire and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Cheshire cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Cheshire. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Cheshire Cottages essential information

Accommodation	70 Cottages
Lowest Price	$92
Highest Price	$192
Popular accommodation	Charming 3 Bedroom Beach Front Cottage, Short Beach Coastal Cottage, Cozy cottage with AC and lake access in charming Connecticut suburb., Direct waterfront cottage on private sandy beach, Modern 4 Bedroom Beach House: Ideal for Families & Long Stays, Guilford Carriage House at Granite Lodge!, Cozy Home near private beach , close to New Haven area colleges Hospitals , Cozy 2-bedroom Cottage with Access to Bantam Lake, New Haven Gem w/ Private Pool, Walk to Beach!