Best Vacation Homes in Litchfield County
Villa
10.0(115 Reviews)
2 Bedrooms
1 Bath
4 Guests
1300 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
US $274/Night
7 Nights - US $1,916
House
10.0(3 Reviews)
1 Bedroom
2 Baths
7 Guests
1840.63 ft²
- Fireplace/Heating
- Balcony/Terrace
View
Pet Friendly
US $437/Night
7 Nights - US $3,057
US $1,700/Night
7 Nights - US $11,897
House
10.0(89 Reviews)
2 Bedrooms
1 Bath
4 Guests
798 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $431/Night
7 Nights - US $3,019
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
2281.95 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Parking
US $430/Night
7 Nights - US $3,010
House
10.0(70 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $362/Night
7 Nights - US $2,536
Apartment
10.0(66 Reviews)
1 Bedroom
1 Bath
2 Guests
625 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $187/Night
7 Nights - US $1,308
Cottage
10.0(57 Reviews)
2 Bedrooms
1 Bath
6 Guests
1350 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $380/Night
7 Nights - US $2,657
Litchfield County Luxury Rentals
House
4 Bedrooms
5 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
Pool- Balcony/Terrace
Unlock the Best Price
House
10.0(13 Reviews)
7 Bedrooms
6 Baths
17 Guests
3650 ft²
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
US $3,191/Night
7 Nights - US $22,339
Villa
6 Bedrooms
3 Baths
10 Guests
215 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Air Conditioner
US $3,190/Night
7 Nights - US $22,327
House
5 Bedrooms
5 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
US $3,105/Night
7 Nights - US $21,735
House
9 Bedrooms
6 Baths
18 Guests
- Hot Tub
Spa- Fireplace/Heating
- Balcony/Terrace
US $3,094/Night
7 Nights - US $21,655
House
10.0(17 Reviews)
5 Bedrooms
4 Baths
10 Guests
4000 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $2,981/Night
7 Nights - US $20,870
House
10.0(4 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,429/Night
7 Nights - US $17,002
Other
4 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $2,338/Night
7 Nights - US $16,368
Litchfield County Pet Friendly Vacation Rentals
House
10.0(54 Reviews)
2 Bedrooms
1 Bath
4 Guests
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $279/Night
7 Nights - US $1,955
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
1905.21 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $323/Night
7 Nights - US $2,259
House
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $1,629/Night
7 Nights - US $11,400
House
10.0(45 Reviews)
2 Bedrooms
2 Baths
4 Guests
1250 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $663/Night
7 Nights - US $4,642
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
204.51 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $235/Night
7 Nights - US $1,644
Cottage
10.0(42 Reviews)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $538/Night
7 Nights - US $3,763
House
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
1500 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $418/Night
7 Nights - US $2,927
House
10.0(14 Reviews)
2 Bedrooms
2 Baths
5 Guests
1300 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $327/Night
7 Nights - US $2,291
Litchfield County Large Vacation Homes
US $1,150/Night
7 Nights - US $8,050
House
10.0(1 Review)
5 Bedrooms
3 Baths
6 Guests
4499.31 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $671/Night
7 Nights - US $4,696
Villa
1 Bedroom
1 Bath
- Internet
- Child Friendly
Barbecue/Outdoor Cooking
Sports/Activities
US $2,357/Night
7 Nights - US $16,498
House
10.0(92 Reviews)
3 Bedrooms
3 Baths
10 Guests
2500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $374/Night
7 Nights - US $2,616
House
9.0(1 Review)
4 Bedrooms
4 Baths
13 Guests
807.29 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $495/Night
7 Nights - US $3,465
House
10.0(52 Reviews)
5 Bedrooms
3 Baths
15 Guests
2500 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,537/Night
7 Nights - US $10,760
House
10.0(52 Reviews)
5 Bedrooms
2 Baths
10 Guests
2200 ft²
- Spa
- Fireplace/Heating
- Pool
- Ocean View
US $997/Night
7 Nights - US $6,977
House
10.0(28 Reviews)
5 Bedrooms
3 Baths
12 Guests
2000 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $564/Night
7 Nights - US $3,949
Why Choose Rent By Owner for your Litchfield County Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Litchfield County
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can greatly enhance your experience, whether you're seeking the vibrant colors of fall or the peacefulness of spring in this scenic region.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, the region experiences warm days perfect for outdoor activities and exploring scenic landscapes, making it an ideal period for booking vacation rentals here.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Early Fall (September to October)
The area offers stunning fall foliage and pleasant weather, attracting visitors seeking a picturesque retreat and comfortable stay in vacation rentals.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Mid Winter (January to February)
In the heart of winter, fewer tourists visit, providing a quieter environment for those booking vacation rentals who prefer a more tranquil experience.
Average Temperature Daytime: 30-40°F - Nighttime: 15-25°F
Late Fall (November to December)
As the region transitions into winter, this period sees reduced visitors, offering serene surroundings and potentially better deals on vacation rentals here.
Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F
Weekly Weather Forecast for Litchfield County
How to Book Your Litchfield County Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Litchfield County
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining areas perfect for al fresco meals surrounded by natural scenery.
- Relax in a private swimming pool that offers a refreshing escape during your stay.
- Take advantage of expansive decks or patios to unwind while soaking in the region's scenic views.
- Explore well-maintained gardens and landscaped yards that enhance the outdoor experience.
- Make the most of fire pits or outdoor fireplaces for cozy evenings under the stars.
- Access dedicated hiking trails or outdoor recreation spaces nearby that showcase the area's natural beauty.
- Utilize spacious lawns, ideal for outdoor activities or family gatherings amidst the region's peaceful surroundings.
Top Attractions Around Litchfield County
What attractions are nearby?
In this charming region, you can enjoy a variety of outdoor activities like hiking, exploring scenic waterfalls, and discovering local parks, all just moments from your chosen vacation rentals in Litchfield County.
Family Activities
- Litchfield County’s Hidden Waterfalls: Discover scenic hikes that lead you to the area's picturesque waterfalls, perfect for family picnics and outdoor exploration.
- Appalachian Trail Adventures: Embark on family-friendly sections of this renowned trail, offering breathtaking views and a chance to connect with nature in the region.
- Farmers Markets and Local Festivals: Enjoy engaging local events and markets that showcase fresh produce, crafts, and entertainment suitable for children and adults alike.
- Historic Villages Exploration: Wander through charming villages filled with historic sites and quaint shops, providing educational and fun experiences for the whole family.
Adult Activities
- Hiking and Outdoor Adventures: Explore the scenic trails and lush landscapes of the region, perfect for reconnecting with nature while enjoying a peaceful hike.
- Visit Historic Sites: Discover the area's rich history through local museums and historic landmarks that provide insight into its cultural heritage.
- Gourmet Dining Experiences: Savor farm-to-table cuisine and artisanal dishes at the area’s acclaimed restaurants, offering a taste of local flavors.
- Cultural Events and Festivals: Attend seasonal festivals and local events that showcase the vibrant arts scene and community spirit here.
Other Places to Stay in Litchfield County, CT
Torrington
Cornwall Bridge
Harwinton
Winsted
New Preston
Lakeville
Litchfield
Litchfield Historic District
Northwest Harwinton
Warren
New Milford
Winchester
Litchfield County Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Outdoor Activities: Take advantage of the region’s scenic trails and lakes for outdoor adventures that perfectly complement your stay in this charming area.
- Visit Authentic Local Shops and Dining: Support local businesses by discovering unique shops and restaurants that showcase the area's vibrant community spirit.
- Plan Your Visit During the Off-Peak Seasons: Experience fewer crowds and more personalized service by scheduling your trip during less busy times in this peaceful destination.
- Choose a Well-Appointed Vacation Rental: Select a property that offers comfort and convenience, enhancing your overall experience in this picturesque part of the region.
Transportation Options
- Car Rentals: Exploring the region is most convenient with a car rental service, offering flexibility to visit charming towns and scenic spots around here.
- Public Transportation: Local bus services provide an economical way to navigate the area, connecting you to key destinations within the region comfortably.
- Taxi and Rideshare Services: Taxis and rideshare options are readily available for quick trips or when you prefer door-to-door transportation in this destination.
- Private Shuttle Services: Private shuttle providers offer tailored transport solutions, making it easier to access popular attractions and amenities nearby.
Local Customs Options
- Farming Heritage: You might notice that the area's long-standing farming traditions influence local festivals and community events in this part of Connecticut.
- Historic Preservation: Respect for historic architecture and preservation efforts play a key role in maintaining the charming character of the region.
- Outdoor Hospitality: Embracing the natural landscape, residents and visitors often participate in outdoor activities, reflecting the region’s appreciation for nature.
- Local Artisanship: Supporting local artisans and craftspeople is common, with markets and shops showcasing handmade goods that highlight regional talent.
Frequently Asked Questions About Litchfield County?
1. What are the top vacation rentals in Litchfield County?
There are a lot of options in Litchfield County. If you plan on staying in the Litchfield County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Litchfield County:
- Charming 1760 Cape Nestled in the Foothills of Litchfield County
- Captivating Artisan Built Home With Spectacular Water Views
- Spacious Home nestled along the Blackberry River in Northwest CT
- Lakefront Summer Stunner in New England Just 2 Hours From NYC
- Charming 1870 cape cottage in Litchfield
- Litchfield Hills Hideaway
- Mountain View Getaway
- Spacious family home with open floor plan.close to lake and clubhouse!
- Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six.
- Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air
2. How many vacation rentals have private pools in Litchfield County?
There are 64 vacation rentals with private pools near Litchfield County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Litchfield County are best for families?
If you are looking for a family-friendly vacation home in Litchfield County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Litchfield County:
4. How many Rentbyowner vacation rentals are available in Litchfield County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 595 in the Litchfield County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Litchfield County.
5. What is the cancellation policy for vacation rentals in this region?
Cancellation policies vary by property, so it’s important to review the specific listing details or contact the owner directly to understand the terms and any applicable fees.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning, service charges, or security deposits are often listed on the property page. Be sure to read the full listing or ask the owner for clarification before confirming your reservation.
7. How do I check the availability of vacation rentals in this destination?
Availability can be checked directly through the listing calendar on the property’s page. If you have specific dates in mind, contacting the owner for confirmation is also recommended.
8. What amenities are typically included with vacation rentals in this part of the country?
Amenities vary by property but commonly include essentials like Wi-Fi, parking, and kitchen facilities. Review each listing carefully to see what is included and reach out if you have specific needs.
9. Is it possible to cancel or modify my booking after I’ve made it?
Cancellation and modification policies depend on the individual property. Contact the owner or review the booking terms provided during the reservation process for detailed options.
Litchfield County Top Rated Vacation Rentals
House
10.0(60 Reviews)
4 Bedrooms
2 Baths
8 Guests
2356 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $486/Night
7 Nights - US $3,403
House
10.0(24 Reviews)
4 Bedrooms
3 Baths
8 Guests
2300 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $975/Night
7 Nights - US $6,822
House
10.0(17 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $685/Night
7 Nights - US $4,794
House
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
1450 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $332/Night
7 Nights - US $2,325
Other
10.0(16 Reviews)
3 Bedrooms
2 Baths
6 Guests
2400 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $308/Night
7 Nights - US $2,158
House
10.0(15 Reviews)
4 Bedrooms
3 Baths
11 Guests
3510 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $949/Night
7 Nights - US $6,641
House
10.0(12 Reviews)
6 Bedrooms
4 Baths
12 Guests
4298 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,379/Night
7 Nights - US $9,652
House
10.0(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $687/Night
7 Nights - US $4,810
