Best Vacation Homes in Litchfield County
1300 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $274/Night
For 7 Nights US $1,916
2281.95 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $430/Night
For 7 Nights US $3,010
US $1,700/Night
For 7 Nights US $11,897
798 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $431/Night
For 7 Nights US $3,019
1840.63 ft²
7 Guests
1 Bedroom
2 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $437/Night
For 7 Nights US $3,057
7 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $362/Night
For 7 Nights US $2,536
625 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $182/Night
For 7 Nights US $1,275
1350 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $380/Night
For 7 Nights US $2,657
Litchfield County Luxury Rentals
12 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
Unlock the Best Price
215 ft²
10 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $3,190/Night
For 7 Nights US $22,327
3650 ft²
17 Guests
7 Bedrooms
6 Bathrooms
Ocean View
House
- Hot Tub
- Ocean View
- Balcony/Terrace
US $3,130/Night
For 7 Nights US $21,909
12 Guests
5 Bedrooms
5 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $3,105/Night
For 7 Nights US $21,735
18 Guests
9 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
US $3,033/Night
For 7 Nights US $21,232
3498.27 ft²
19 Guests
7 Bedrooms
8 Bathrooms
Free Cancellation
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $2,825/Night
For 7 Nights US $19,775
12 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,401/Night
For 7 Nights US $16,809
8 Guests
4 Bedrooms
3 Bathrooms
Group Friendly
Other
US $2,338/Night
For 7 Nights US $16,368
Litchfield County Pet Friendly Vacation Rentals
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $279/Night
For 7 Nights US $1,955
1905.21 ft²
6 Guests
1 Bedroom
3 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $323/Night
For 7 Nights US $2,259
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,629/Night
For 7 Nights US $11,400
1250 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $622/Night
For 7 Nights US $4,355
1496.18 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Spa
- Pet Friendly
- Parking
US $250/Night
For 7 Nights US $1,750
1100 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $522/Night
For 7 Nights US $3,653
1500 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $418/Night
For 7 Nights US $2,926
1800 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $369/Night
For 7 Nights US $2,583
Litchfield County Large Vacation Homes
10 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Child Friendly
- Security/Safety
US $1,150/Night
For 7 Nights US $8,050
4499.31 ft²
6 Guests
5 Bedrooms
3 Bathrooms
House
- Oceanfront
- Fireplace/Heating
- Pool
US $671/Night
For 7 Nights US $4,696
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Internet
- Child Friendly
- Barbecue/Outdoor Cooking
US $2,357/Night
For 7 Nights US $16,498
2500 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $362/Night
For 7 Nights US $2,536
807.29 ft²
13 Guests
4 Bedrooms
4 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $495/Night
For 7 Nights US $3,465
2500 ft²
15 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,227/Night
For 7 Nights US $8,589
2200 ft²
10 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Spa
- Fireplace/Heating
- Pool
US $713/Night
For 7 Nights US $4,989
1400 ft²
12 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,308/Night
For 7 Nights US $9,157
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
Lakeville
Litchfield Historic District
Northwest Harwinton
New Milford
Warren
Roxbury
Litchfield
Goshen
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.
Litchfield County Vacation Rental Frequently Asked Questions
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 Winter Wonderland 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 and fireplace.close to ski area!
- 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 65 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 590 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
2356 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
US $463/Night
For 7 Nights US $3,238
2300 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $737/Night
For 7 Nights US $5,156
4000 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,349/Night
For 7 Nights US $9,442
12 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $590/Night
For 7 Nights US $4,133
1450 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $285/Night
For 7 Nights US $1,993
2400 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $366/Night
For 7 Nights US $2,560
3510 ft²
11 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $886/Night
For 7 Nights US $6,199
4298 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,122/Night
For 7 Nights US $7,857
