Book Holiday Homes in Litchfield

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Featured Holiday Homes in Litchfield

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

New Fairfield
Book a stay at this family-friendly vacation home in New Fairfield. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Squantz Pond State ...
Opens in a new windowLakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Charming 1870 cape cottage in Litchfield

Charming 1870 cape cottage in Litchfield

Litchfield
Stay at this vacation home in Litchfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions White Memorial Conservation Center and Bantam ...
Opens in a new windowCharming 1870 cape cottage in Litchfield
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

New Fairfield
Stay at this vacation home in New Fairfield. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Squantz Pond State Park and Candlewood Lake ...
Opens in a new windowLakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
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Bluebird Valley Farmhouse

Bluebird Valley Farmhouse

Millerton
Stay at this vacation home in Millerton. Enjoy a garden, laundry facilities, and patios. Popular attractions Harlem Valley Rail Trail and Veterans Field are ...
Opens in a new windowBluebird Valley Farmhouse
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
Stay at this vacation home in Sheffield. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Drury Preserve and Lime Kiln Farm Wildlife Sanctuary ...
Opens in a new windowCheerful 3-bedroom cottage with woodstove
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

New Milford
Stay at this vacation home in New Milford. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Elephant's Trunk Flea Market and Valley ...
Opens in a new windowLand’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

New Britain
The price is NZ$513 per night from 27 Oct to 28 Oct
NZ$513
27 Oct - 28 Oct
includes taxes & fees
Stay at this vacation home in New Britain. Enjoy a fitness center, laundry facilities, and air conditioning. Popular attractions New Britain Stadium and New ...
Opens in a new windowClean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds
Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway

Goshen
The price is NZ$2,103 per night from 6 Oct to 7 Oct
NZ$2,103
6 Oct - 7 Oct
includes taxes & fees
Stay at this vacation home in Goshen. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mohawk State Forest and Goshen Historic District ...
Opens in a new windowWhispering Estate Guest House - A Romantic Countryside Getaway
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Harwinton
Stay at this vacation home in Harwinton. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Harwinton Conservation and Recreation Area and ...
Opens in a new windowCharming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
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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.

Litchfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Litchfield vacation homes are the perfect way for you to wing it.

Holiday houses in Litchfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Litchfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Litchfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Litchfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Litchfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Litchfield Holiday Homes essential information

Accommodation
294 Holiday Homes
Lowest Price
NZ$185
Highest Price
NZ$2,103
Popular accommodation
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed, Charming 1870 cape cottage in Litchfield, Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!, Bluebird Valley Farmhouse, Cheerful 3-bedroom cottage with woodstove, Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT, Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds, Whispering Estate Guest House - A Romantic Countryside Getaway, Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Top trending hotels in Litchfield

The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road, Litchfield, CT
Fully refundableReserve now, pay when you stay
The price is NZ$627 per night from 30 Sept to 1 Oct
NZ$627
30 Sept - 1 Oct
includes taxes & fees
Stay at this 4-star spa hotel in Litchfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition ...
Opens in a new windowThe Litchfield Inn
The Abner Hotel

The Abner Hotel

3 out of 5
15 West St, Litchfield, CT
The price is NZ$645 per night from 19 Oct to 20 Oct
NZ$645
19 Oct - 20 Oct
includes taxes & fees
Stay at this 3-star hotel in Litchfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Litchfield Town Green and Litchfield Historical ...
Opens in a new windowThe Abner Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
The price is NZ$239 per night from 26 Oct to 27 Oct
NZ$239
26 Oct - 27 Oct
includes taxes & fees
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 ...
Opens in a new windowHoliday Inn Express Southington by IHG
Save an average of 15% on thousands of hotels when you're signed in
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is NZ$185 per night from 26 Oct to 27 Oct
NZ$185
26 Oct - 27 Oct
includes taxes & fees
Stay at this 3-star business-friendly hotel in Southbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Opens in a new windowWyndham Southbury
Don't see what you're looking for?
See all available properties in Litchfield
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.