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Litchfield Holiday Rentals

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Holiday Rentals in Litchfield

The Jefferson Guest House, Spacious, Special Views
10.0 out of 10, Exceptional, (7)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
The price is AU$548
includes taxes & fees
16 Oct - 17 Oct
The Jefferson Guest House, Spacious, Special Views
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
9.4 out of 10, Exceptional, (30)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
10.0 out of 10, Exceptional, (2)
"This is a property that is very good for large family gatherings, which is how we gathered for a birthday celebration. This area of CT. is great and has lots to do.The house is in the perfect location to do all of it.Again, suits large groups well. Room for everyone."
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
8.6 out of 10, Excellent, (26)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
The Goshen Glass Chalet
9.6 out of 10, Exceptional, (40)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
The Goshen Glass Chalet
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (5)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
The price is AU$441
includes taxes & fees
15 Oct - 16 Oct
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
The Sun Filled Cozy Creamery
8.8 out of 10, Excellent, (22)
"Nice,cozy and a reasonable rate."
The price is AU$426
includes taxes & fees
18 Oct - 19 Oct
The Sun Filled Cozy Creamery
Summer Lake Cottage, private beach, Berkshire Hills, small village
9.4 out of 10, Exceptional, (83)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
9.4 out of 10, Exceptional, (9)
"Needed a place to sleep for a couple of nights and this worked for us."
The price is AU$271
includes taxes & fees
15 Oct - 16 Oct
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Lakefront Fall Foliage in New England Just 2 Hours From NYC
10.0 out of 10, Exceptional, (84)
"Great location and fully equipped cabin! I hope to return sometime soon Everything was perfect!"
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is AU$1,109
includes taxes & fees
26 Oct - 27 Oct
Guesthouse Cabin vacation rentals in Berkshire County
Antique Farmhouse Totally Restored
9.8 out of 10, Exceptional, (92)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored
Candlewood Lake Retreat; Dock, Game Room & Firepit
10.0 out of 10, Exceptional, (47)
"Everything was great! Thank you!"
The price is AU$1,982
includes taxes & fees
16 Oct - 17 Oct
Candlewood Lake Retreat; Dock, Game Room & Firepit
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (11)
"Everything was great...and beautiful!"
The price is AU$626
includes taxes & fees
20 Oct - 21 Oct
The Blue Elm - A Historic Berkshire Cottage
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
10.0 out of 10, Exceptional, (5)
"Everything was amazing "
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
9.6 out of 10, Exceptional, (14)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Cozy Safe Home
The price is AU$608
includes taxes & fees
15 Oct - 16 Oct
Cozy Safe Home
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford
10.0 out of 10, Exceptional, (7)
"We were in town for a family wedding and found this quaint little apartment that was quiet and secluded. Being on the river we did find a lot of bugs, but nothing we couldnt handle. The owners were extremely nice and responsive and we had a wonderful stay. "
Charming 2-bedroom apartment waterfront with WiFi, lovely New Milford
Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
10.0 out of 10, Exceptional, (11)
"Wonderful "
Escape to a Luxury Lakehouse Retreat- Chefs Indoor Outdoor Kitchen Hot Tub Steam
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (51)
"It has stairs to climb up to apartment. Everything was lovely.And the owners go out of their way to make you feel welcome."
Private Annex/Former Artist Studio
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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Top Litchfield Hotel Reviews

Find out more about Litchfield

Everything you need to know about Litchfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Litchfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Litchfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Litchfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Litchfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Litchfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Litchfield holiday rentals we have selected for you start as low as AU$271 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Litchfield rentals

At Expedia, we put the best Litchfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Litchfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Litchfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Litchfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Litchfield?

Yes, there are holiday rentals in Litchfield close to White Memorial Conservation Center, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Litchfield has a good selection of restaurants. Make sure you have time to check out the golf courses and wineries during your trip.

What are some of the best holiday rentals that Litchfield has to offer?

Lakefront Fall Foliage in New England Just 2 Hours From NYC: This holiday home rental outside of Litchfield is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a private garden and a selection of games.

How many holiday rentals will I find in Litchfield?

Choose from 15 Expedia holiday rentals in Litchfield for a memorable holiday.

What’s there to see and do in Litchfield?

Cultural attractions include White Memorial Conservation Center and Tapping Reeve House and Law School, whereas Litchfield Town Green and Bantam Lake are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Mount Tom State Park and Mohawk Mountain State Forest.

What’s a holiday rental in Litchfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Litchfield. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.