Vacation rentals in Litchfield

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Top-rated vacation rentals in Litchfield

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Top guest favorite
A cozy living area features a light-colored sofa adorned with red accent pillows. A wooden coffee table sits in the center, accompanied by a vintage armchair and a small desk. Warm lighting is provided by a floor lamp, with simple wall art enhancing the inviting space.
Home in Torrington
4.99 out of 5 average rating, 112 reviews

Country living at it's finest

Cozy country home. Quiet and serene; a great place for a get away in Litchfield County Connecticut. An ideal location ,Torrington is about 2 1/2 hours from Boston and NYC and convenient to the Berkshires. Within driving distance to various outdoor activities and attractions including hiking trails, breweries, distillery, wineries, skiing, golf antique shopping, restaurants and variety of entertainment . The hosts are accessible for directions, assistance, or a fun history lesson of the area.

Top guest favorite
A well-maintained garden is framed by a wooden fence, featuring vibrant sunflowers and lush greenery. The manicured lawn surrounds the garden, creating a serene outdoor space. Towering trees provide a natural backdrop, enhancing the peaceful ambiance of the area.
Guest suite in Litchfield
4.96 out of 5 average rating, 140 reviews

Country Suite

Situated above a charming residential barn this cozy two room suite offers comfort and privacy for those traveling through bucolic Litchfield CT This airy loft boasts WiFi cable TV a hi-tech key free security lock automatic outside lighting A large bedroom overlooks the front of the property in this quiet wooded neighborhood large enough to have a king size bed large bathroom work space and kitchenette Keurig and coffee incl. The front room faces a sweeping lawn on this well kept property

Top guest favorite
A cozy living room features a comfortable gray sofa adorned with colorful cushions, accompanied by a wooden coffee table. Two chairs, one with burgundy upholstery and the other with a light wood finish, add seating options. Soft lighting is provided by two table lamps and recessed lights.
Apartment in Litchfield
4.99 out of 5 average rating, 153 reviews

Litchfield Hills Hideaway

Enjoy the Litchfield Hills from this newly renovated one bedroom apartment with private entrance. Amenities include full kitchen, living room, bedroom with queen bed, and full en suite bathroom. WiFi and cable TV included. All located less than 2 miles from historic Litchfield Center. Our property borders on the White Memorial Foundation nature preserve, with over 40 miles of hiking trails. Mohawk Mountain Ski area in Cornwall and Ski Sundown in New Hartford are only a short drive away.

Top guest favorite
The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.
Home in Cornwall
4.98 out of 5 average rating, 165 reviews

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

Top guest favorite
A vibrant garden filled with blooming flowers is framed by a well-maintained pathway leading to a red two-story building. Steps ascend through the landscaping, which features a variety of plants and foliage, enhancing the serene outdoor setting.
Apartment in Litchfield
4.99 out of 5 average rating, 208 reviews

Artist's Garden Apartment

Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

Guest favorite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 434 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Guest favorite
The charming cottage, with its white siding and red door accents, is set amidst lush greenery. A well-maintained yard features grass and flowering plants, while a stone wall frames the scene, adding to the property's rustic appeal.
Cottage in Litchfield
4.87 out of 5 average rating, 399 reviews

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

This vintage style cottage offers guests a comfortable and convenient stay in Litchfield with it’s range of amenities. Essential amenities include air conditioning, cooking basics, a dedicated workspace, dishes and silverware, a dryer, hair dryer, heating, hot tub, kitchen, TV, washer, and Wi-Fi. 5 Min - Litchfield Town center 9 Min - Arethusa Dairy farm- Restaurant 10 Min - White Memorial Conservation Center 8 Min - Bantam Lake 19 Min - Mohawk Mountain Ski Area

Top guest favorite
A spacious room features a comfortable bed with a light blue quilt, complemented by decorative pillows. A desk and chair are positioned by a window, with bookshelves in the background. Natural light filters through the windows, creating a welcoming atmosphere.
Guest suite in Morris
4.98 out of 5 average rating, 439 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own lounging/dining area. Guests have their own separate entrance & parking space(s). Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing & just 10 minutes to Washington Depot. We've recently made some updates in response to guests' feedback!

Top guest favorite
Apartment in Litchfield
4.97 out of 5 average rating, 153 reviews

The Litchfield Nook - Cozy Uptown Apartment

Welcome to a cozy and peaceful nook in the hills! This well appointed apartment provides a home away from home feel. The unit is located on the first floor of a multi unit family house and sleeps 4 comfortably. You will be within walking distance to the iconic Litchfield Green and White Memorial Foundation. Everything that there is to see and do in Litchfield is within a short driving distance. Enjoy the beauty of Litchfield and come join us as our guest!

Top guest favorite
An aerial view captures a sprawling farm landscape at sunset, with the sun dipping behind rolling hills. The guest house, white with a gray roof, is surrounded by green fields and lush vegetation, creating a serene atmosphere.
Farm stay in New Milford
5 out of 5 average rating, 130 reviews

Farm House

A serene get away in a farm cottage on a real working farm. We homesteaded this property in 2012 and have created our own slice of paradise. We grow produce and flowers that is sold at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, and chickens. You're welcome to roam the property, sit by the pond, visit with the animals, take a tour of the farm or explore all that Litchfield county has to offer!

Top guest favorite
A view of a classic farmhouse, surrounded by green grass and trees. Hay is scattered across the foreground, and the house features a porch with visible outdoor seating. A quiet road is seen in the distance, offering a glimpse of the serene rural setting.
Home in Bethlehem
4.98 out of 5 average rating, 320 reviews

Litchfield County Farmhouse with a Modern Twist

Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

Top guest favorite
A Craftsman-style home is surrounded by lush green lawns and gardens, featuring a warm, inviting facade. The structure includes a mix of gabled roofs and large windows, with a stone patio that presents outdoor seating. Copious trees provide natural shade, enhancing the tranquil setting.
Home in Litchfield
4.96 out of 5 average rating, 105 reviews

Home in historic Litchfield village

An enjoyable, easy 10 minute walk to the town center for shops & restaurants. A Craftsman Style home, it is casual & comfortable. Though private, we have neighbors that border our property. Guests best suited to our home would be small families or 2 or 3 couples looking for a very quiet small town getaway or a place to call home for a special event in the area. Please note 2 night minimum required and property to be used only by registered guests.

Popular amenities for Litchfield vacation rentals

When is the best time to visit Litchfield?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$53,272 GYDG$50,138 GYDG$48,049 GYDG$49,512 GYDG$54,943 GYDG$62,673 GYDG$62,673 GYDG$66,015 GYDG$59,539 GYDG$63,091 GYDG$55,988 GYDG$57,868 GYD
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Frequently Asked Questions

  • What are the best places to stay in Litchfield?

    Many guests choose vacation rentals near the Litchfield Historic District for easy access to shops, dining, and cultural attractions. The countryside outside the center has cottages and farmhouse-style stays for a peaceful setting.

  • What are the best things to do in Litchfield with kids?

    Kids can explore nature at White Memorial Conservation Center, try pond-dipping or wildlife watching, and enjoy picnicking by Lake Bantam. Interactive exhibits at the Litchfield History Museum engage visitors of all ages.

  • What are some of the best things to do in Litchfield?

    Explore Litchfield’s preserved historic district, wander nature trails at White Memorial Conservation Center, and visit boutique shops or local art galleries. The area also has gardens and small museums reflecting regional heritage.

  • How is the weather in Litchfield?

    Litchfield has cold winters, with temperatures ranging from 16–35°F (-9–1°C) in January, and warm summers near 59–82°F (15–28°C) in July. Rainfall is spread throughout the year, so packing layers and a waterproof jacket is helpful.

  • When is the best time to visit Litchfield?

    Late spring through early fall is often recommended for milder temperatures and local festivals. Fall brings colorful foliage, while summer has outdoor events and access to area lakes.

  • What are the best places to visit in Litchfield?

    Often recommended spots in Litchfield include the Litchfield Historic District, the Litchfield History Museum, and White Memorial Conservation Center. Visiting area gardens and Lake Bantam is also suggested by locals.

  • What are some hiking trails in Litchfield?

    Litchfield has a variety of nature trails, with many found at White Memorial Conservation Center and Topsmead State Forest. Both locations are often suggested for gentle walks, birdwatching, and forest scenery.

  • What are some family activities we can do in Litchfield?

    Families are encouraged to explore White Memorial Conservation Center for nature walks, enjoy picnicking at Lake Bantam, and visit the Litchfield History Museum for hands-on exhibits. Seasonal outdoor activities like kayaking and maple sugaring are also popular.

  • What are some of the best day trip ideas from Litchfield?

    From Litchfield, explore local vineyards, nearby state parks, or towns known for antique shops and regional art. Farm tours and seasonal flower fields can be found around the surrounding countryside.

  • Are there any pet friendly accommodations available in Litchfield?

    Many accommodations in Litchfield welcome pets, especially home and cabin rentals around the countryside. Several parks and trails, like those at White Memorial Conservation Center, make outings with dogs enjoyable.

  • What are some local tips for visiting Litchfield?

    Litchfield has walkable streets, so comfortable footwear helps when exploring historic areas and parks. Many local shops, galleries, and farmers markets feature items crafted by area artists and growers.

  • What is Litchfield known for?

    Litchfield is known for its well-preserved colonial architecture, lush countryside, and scenic walking trails. The town’s history and arts community are reflected in its museums, galleries, and seasonal events.

  • What are the best hidden gems to explore in Litchfield?

    Many enjoy wandering the trails of Topsmead State Forest, exploring small art galleries, or discovering historic cemeteries around the town. Maple sugaring demonstrations and local gardens offer quieter experiences.

  • What are the best foods to try in Litchfield?

    Litchfield’s food scene highlights New England staples like fresh-baked breads, locally sourced cheeses, and produce from regional farms. Some area restaurants also feature maple treats and seasonal pies.

  • What should I bring for a trip to Litchfield?

    Bring comfortable shoes for exploring, layers for shifting temperatures, and rain gear, especially in spring or fall. If you plan to spend time on trails or at the lake, insect repellent and sunscreen are also useful.

  • What is the nightlife in Litchfield like?

    Litchfield’s nightlife is relaxed, with casual wine bars, neighborhood pubs, and a few spots for live music around the town center. Evenings often focus on conversation and locally inspired food and drink.

  • What are the most popular events or festivals in Litchfield?

    Litchfield frequently hosts outdoor concerts and art fairs in the summer, as well as holiday parades and craft festivals in late fall. The town green is a popular gathering place for these seasonal events.

  • Are there family friendly vacation rentals in Litchfield?

    Litchfield has a selection of family friendly rentals, including homes with outdoor space or proximity to parks and nature trails. Many options are near the historic center and recreational sites, making it easy to explore together.

Quick stats about vacation rentals in Litchfield

  • Total vacation rentals

    Explore 140 vacation rentals in Litchfield

  • Nightly prices starting at

    Litchfield vacation rentals start at G$14,624 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,970 verified reviews to help you choose

  • Family-friendly vacation rentals

    100 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Vacation rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    140 of Litchfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Litchfield rentals

  • 4.9 Average rating

    Litchfield stays are highly rated by guests—averaging 4.9 out of 5!