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Litchfield Holiday Rentals

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Check prices for these dates

Tonight
31 Oct - 1 Nov
Tomorrow
1 Nov - 2 Nov
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Holiday Rentals in Litchfield

Pool
Charming 1870 cape cottage in Litchfield
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (64)
"Beautiful house"
United States
Anonymous traveller
Charming 1870 cape cottage in Litchfield
2 bedrooms, desk, iron/ironing board, WiFi
The Jefferson Guest House, Spacious, Special Views
The Jefferson Guest House, Spacious, Special Views
10.0 out of 10, Exceptional, (8)
"This is a beautiful property. The property owners were very welcoming and prompt to answer any questions and concerns. Litchfield is a wonderful little town that has so much to offer. We can’t wait to go back. "
United States
J D.
The price is HK$2,266
HK$2,910 total
includes taxes & fees
2 Nov - 3 Nov
The Jefferson Guest House, Spacious, Special Views
Outdoor dining
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
9.4 out of 10, Exceptional, (30)
"Only thing that was a challenge was carrying the kayaks down the hill and across the street. Living room was a bit hot due to no air conditioner. Host was extremely nice and accomodating and the place was well kept. "
United States
Jennifer W.
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Exterior
New One Bedroom Apartment Centrally Located in Southbury
New One Bedroom Apartment Centrally Located in Southbury
9.8 out of 10, Exceptional, (16)
"Excellent stay !!!! Everything was perfect. Communication was phenomenal.!!!!"
United States
daniellle
The price is HK$699
HK$960 total
includes taxes & fees
3 Nov - 4 Nov
New One Bedroom Apartment Centrally Located in Southbury
Dining
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
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."
United States
Paula R.
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
10.0 out of 10, Exceptional, (7)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
United States
Lara S.
The price is HK$874
HK$1,914 total
includes taxes & fees
3 Nov - 4 Nov
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
Dining
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
8.6 out of 10, Excellent, (26)
"Clean, quite stores only 8 minutes away. "
United States
Mindy H.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
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."
United States
James (Jim) L.
The price is HK$734
HK$1,357 total
includes taxes & fees
4 Nov - 5 Nov
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Exterior
Summer Lake Cottage, private beach, Berkshire Hills, small village
Summer Lake Cottage, private beach, Berkshire Hills, small village
9.4 out of 10, Exceptional, (84)
"Wonderful lake retreat 🥾"
United States
Elizabeth B.
Summer Lake Cottage, private beach, Berkshire Hills, small village
TV, fireplace
Southbury Charming Studio Retreat on Beautiful Grounds — Sleeps 4
Southbury Charming Studio Retreat on Beautiful Grounds — Sleeps 4
10.0 out of 10, Exceptional, (1)
"Our stay was perfect! The studio was lovely with many nice touches. We woke up to beautiful views of the property. Our hosts were friendly and helpful. Would absolutely stay here again!"
United States
Tara F.
Southbury Charming Studio Retreat on Beautiful Grounds — Sleeps 4
Outdoor dining
The Sun Filled Cozy Creamery
The Sun Filled Cozy Creamery
8.8 out of 10, Excellent, (23)
"Pleasure staying here. "
United States
Jesse H.
The price is HK$645
HK$2,134 total
includes taxes & fees
2 Nov - 3 Nov
The Sun Filled Cozy Creamery
Outdoor dining
The Goshen Glass Chalet
The Goshen Glass Chalet
9.6 out of 10, Exceptional, (41)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
United States
Tracy F.
The Goshen Glass Chalet
Outdoor dining
Fun Downtown Location 2nd flr
Fun Downtown Location 2nd flr
9.8 out of 10, Exceptional, (77)
"Nice place, comfy beds, good amenities, clean. Good restaurants."
United States
Tanya C.
Fun Downtown Location 2nd flr
Dining
Guesthouse Cabin vacation rentals in Berkshire County
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
United States
Robert B.
The price is HK$3,030
HK$5,355 total
includes taxes & fees
4 Nov - 5 Nov
Guesthouse Cabin vacation rentals in Berkshire County
Exterior
The Blue Elm - A Historic Berkshire Cottage
The Blue Elm - A Historic Berkshire Cottage
10.0 out of 10, Exceptional, (12)
"If I could have given it more than 5 stars I would have. Beautiful, quiet area and the place is stunning. The gas fireplace in the dining area was great, has pretty much everything you could need and incredibly stylish (the retro fridge and microwave were very cool). Can’t speak to the pullout but the king in the master might have been the most comfortable bed I’ve ever slept in and the double shower is awesome. The hosts were friendly and responsive. Went to hike and the number of trails within...
United States
Marc R.
The price is HK$1,398
HK$2,994 total
includes taxes & fees
4 Nov - 5 Nov
The Blue Elm - A Historic Berkshire Cottage
Microwave, oven, stovetop, dishwasher
Spacious 3-Bedroom Home Awaits - Designed for Comfort & Relaxation!!!
Spacious 3-Bedroom Home Awaits - Designed for Comfort & Relaxation!!!
Spacious 3-Bedroom Home Awaits - Designed for Comfort & Relaxation!!!
Exterior
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
9.6 out of 10, Exceptional, (15)
"It was a great time. Loved it hear would come back again. Owner was very helpful."
United States
Nosa I.
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Fridge, microwave, oven, stovetop
Cozy Safe Home
Cozy Safe Home
The price is HK$1,804
HK$3,100 total
includes taxes & fees
11 Nov - 12 Nov
Cozy Safe Home
Outdoor dining
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!
8.8 out of 10, Excellent, (24)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
United States
Kevin P.
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Outdoor dining
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
10.0 out of 10, Exceptional, (11)
"From check-in to check-out, everything at the yellow cottage was wonderful! Jessica, the host, was lovely, and quite accommodating. She ensured that our every need was met. The cottage is beautifully appointed, very well-equipped, and extremely comfortable. The lake setting is idyllic.We have had a perfect getaway - and have already booked our next stay! "
United States
KIMBERLY D.
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
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

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"Yes"
Armin 2-night trip
Posted 8 hours ago
Wyndham Southbury

Find out more about Litchfield

Search for holiday rentals in Litchfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Litchfield using one of the methods below:

  • View our selection of featured holiday rentals in Litchfield
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  • Enter your travel dates to view the best deals on holiday rentals in Litchfield while they last

Look no further and take a look at our great range of rental properties in Litchfield!

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?

Charming 1870 cape cottage in Litchfield: This highly rated holiday home rental in Litchfield offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a garden.

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.