Hot Cheshire Cottage Rates

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Featured Cottages in Cheshire

Beachside Branford- walk t0 Beach, Grill, Fire Pit

Beachside Branford- walk t0 Beach, Grill, Fire Pit

Branford
With a stay at this cottage in Branford (Pine Orchard), you'll be within a 15-minute drive of Yale University and Stony Creek Brewery.
Beachside Branford- walk t0 Beach, Grill, Fire Pit
Guilford Carriage House at Granite Lodge!

Guilford Carriage House at Granite Lodge!

Guilford
Located in Guilford, this cottage is by the sea, within a 10-minute drive of Bill Miller’s Castle and Orchard Hill Plaza Shopping Center.
Guilford Carriage House at Granite Lodge!
Cozy 2-bedroom Cottage with Access to Bantam Lake

Cozy 2-bedroom Cottage with Access to Bantam Lake

Morris
With a stay at this cottage in Morris, you'll be on a lake, just steps from Bantam Lake and a 2-minute drive from Camp Columbia State Park.
Cozy 2-bedroom Cottage with Access to Bantam Lake
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Family Friendly Cottage for 8 with Arcade Games!!

Family Friendly Cottage for 8 with Arcade Games!!

New Haven
With a stay at this cottage in East Haven (East Shore), you'll be within a 10-minute drive of Yale University and Yale-New Haven Hospital.
Family Friendly Cottage for 8 with Arcade Games!!
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Plymouth
Located in Plymouth, this cottage is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

Bethlehem
When you stay at this cottage in Bethlehem, you'll be on a lake, within a 5-minute drive of Bellamy-Ferriday House and Garden and Old Bethlehem Historical Society ...
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

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

West Haven
When you stay at this cottage in West Haven, you'll be by the sea, within a 5-minute drive of Yale University and Yale-New Haven Hospital.
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
The Dream Location for Your Perfect Vacation

The Dream Location for Your Perfect Vacation

Branford
Located in Branford, this cottage is by the ocean, within a 10-minute drive of Stony Creek Brewery and Stony Creek - Thimble Islands Historic District.
The Dream Location for Your Perfect Vacation
Direct waterfront cottage on private sandy beach

Direct waterfront cottage on private sandy beach

East Haven
With a stay at this cottage in East Haven (Morgan Point), you'll be within a 15-minute drive of Yale University and Yale-New Haven Hospital.
Direct waterfront cottage on private sandy beach
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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.

Cheshire Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Cheshire will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Cheshire definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Cheshire, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Cheshire Cottages essential information

Accommodation
68 Cottages
Lowest Price
AU$129
Highest Price
AU$215
Popular accommodation
Beachside Branford- walk t0 Beach, Grill, Fire Pit, Guilford Carriage House at Granite Lodge!, Cozy 2-bedroom Cottage with Access to Bantam Lake, Family Friendly Cottage for 8 with Arcade Games!!, Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape, Lakeview property in private community. Lake & beach access. Swim/Kayak all day!, Modern 4 Bedroom Beach House: Ideal for Families & Long Stays, The Dream Location for Your Perfect Vacation , Direct waterfront cottage on private sandy beach

Top trending hotels in Cheshire

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
64 Knotter Dr, Cheshire, CT
Fully refundable
The price is AU$195 per night from 13 Apr to 14 Apr
AU$195
includes taxes & fees
13 Apr - 14 Apr
Located in Cheshire, Holiday Inn Cheshire - Southington by IHG is a 4-minute drive from Mount Southington Ski Area and 6 minutes from Barker Character, Comic ...
Holiday Inn Cheshire - Southington by IHG
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
The price is AU$129 per night from 24 Apr to 25 Apr
AU$129
includes taxes & fees
24 Apr - 25 Apr
With a stay at Cheshire Welcome Inn in Cheshire, you'll be within a 10-minute drive of Quinnipiac University and Bartlem Park.
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 AU$215 per night from 20 Apr to 21 Apr
AU$215
includes taxes & fees
20 Apr - 21 Apr
New Haven Hotel is centrally located in New Haven, a 4-minute walk from Shubert Theater and 5 minutes by foot from New Haven Green.
New Haven Hotel
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The Capitol Hotel, Ascend Hotel Collection

The Capitol Hotel, Ascend Hotel Collection

3 out of 5
440 Asylum St, Hartford, CT
A stay at The Capitol Hotel, Ascend Hotel Collection places you in the heart of Hartford, just a 4-minute walk from XL Center and within a 5-minute drive of ...
The Capitol Hotel, Ascend Hotel Collection
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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.

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^Subject to availability and chosen travel dates.