Vacation Rentals in Litchfield, CT

177 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Litchfield, CT holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

177 Holiday rentals and Airbnb in Litchfield, CT

Best family friendly Litchfield, CT holiday rentals

Among the 177 accommodations in Litchfield, CT, here are the 4 best family friendly rentals

Jim & Pats Litchfield Hills Lookout On 4.3 Acres - Litchfield, CT
9.9 20 reviews

Jim & Pats Litchfield Hills Lookout On 4.3 Acres

apartment, Morris
This three-bedroom apartment is located on Looking Glass Hill, a quiet road just 8 kilometres from the centre of Bantam and Bantam Lake. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment comfortably sleeps up to eight guests and offers a range of amenities, including a fully equipped kitchen, a spacious living area with a fireplace, and a private garden with a deck and a gas grill. Guests can enjoy scenic views of Mount Tom and the Litchfield Hills, as well as access to walking trails and a nearby sister property for larger groups.
Gather Your Family At This Country Estate - Litchfield, CT
9.0 29 reviews

Gather Your Family At This Country Estate

apartment, Watertown
This rural property in Watertown offers excellent access to recreational parks and is within driving distance of historical sites such as the Old Bethlehem Historical Society Museum and Bellamy-Ferriday House and Garden.
This spacious 324 square meter flat accommodates up to 14 guests with 6 bedrooms and 2 bathrooms, featuring a jacuzzi, spa, garden, and parking, with nearby winter activities including snowboarding and skiing.
Peaceful Riverfront Family Retreat, Litchfield Ct - Litchfield, CT
10 15 reviews

Peaceful Riverfront Family Retreat, Litchfield Ct

apartment, Litchfield
This secluded woodland retreat is situated in Litchfield, Connecticut, just 16 kilometres from shops and wineries and 160 kilometres from New York City.
The house is a spacious four-bedroom property with three bathrooms, comfortably accommodating up to ten guests. It offers a range of amenities, including a chef's kitchen, a private river for swimming and crawfishing, and a kiddie pool and play structure for younger guests.
Bespoke Litchfield - Family Friendly, Hot Tub - Litchfield, CT
10 2 reviews

Bespoke Litchfield - Family Friendly, Hot Tub

apartment, Litchfield
This Litchfield Hills retreat in Bantam, CT, offers a spacious five-bedroom, three-and-a-half-bathroom house, ideal for families, located a 10-minute drive from Bantam Lake and a 5-minute drive from Mount Tom State Park.
This property boasts 313 square meters of living space, accommodating up to 14 guests with a fully equipped kitchen, air conditioning, a hot tub, a fire pit, an arcade/game room with a pool table and PAC-MAN, and ample parking for six cars, all within a two-hour drive of London.

Best Litchfield, CT holiday rentals with a balcony

Peaceful Goshen Cottage W/ Screened Porch & Views! - Litchfield, CT
No reviews

Peaceful Goshen Cottage W/ Screened Porch & Views!

house, Goshen
House listing. You will be in Goshen.
Facilities and services include a fridge, air conditioning and a washing machine. Take advantage of the Free Parking with this accommodation.
Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy - Litchfield, CT
10 4 reviews

Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy

house, Bethlehem
This Bethlehem holiday home, located near the Abbey of Regina Laudis (3.4km) and Flanders Nature Centre (4.7km), offers a peaceful woodland retreat.
The 171 square metre property boasts one bedroom, two bathrooms, sleeps thirteen guests, and includes a fully equipped kitchen, spa, terrace, garden, free Wi-Fi, parking, and outdoor play equipment.
Lakefront Cottage W/dock, Kayaks - Litchfield, CT
No reviews

Lakefront Cottage W/dock, Kayaks

apartment, Morris
This lakehouse in Morris offers exclusive private lakefront access on Bantam Lake, Connecticut's largest freshwater lake, and is located within 5 kilometres of Topsmead State Forest, the Litchfield Historical Society Museum and the White Memorial Conservation Centre.
This 3-bedroom apartment accommodates up to 6 guests and features a newly renovated game room, a washer and dryer, and a large parking lot with electric vehicle charging, whilst offering direct access to swimming, kayaking, biking, and hiking activities.
Steele Brook Manor Tranquil Get Away Nestled  In  Litchfield County. - Litchfield, CT
9.2 5 reviews

Steele Brook Manor Tranquil Get Away Nestled In Litchfield County.

apartment, Watertown
This family-friendly Watertown apartment, near Black Rock State Park (approx. 26km) and Union Station (approx. 18km), offers convenient access to both natural beauty and urban amenities.
The two-bedroom, one-bathroom dwelling sleeps six, boasting a fully equipped kitchen, in-unit laundry, a terrace, and access to a garden and spa; nearby attractions include The Christmas Shop and Glebe House Museum.

Frequently asked questions about holiday rentals in Litchfield, CT

  • What are the must-see sights in Litchfield, Connecticut?

    Litchfield boasts several must-see attractions. The Litchfield Historical Society Museum offers a fascinating glimpse into the town's rich past. The stunning Litchfield Green, a picturesque village square, is perfect for a stroll. For architecture buffs, the elegant First Congregational Church and the Tapping Reeve House and Litchfield Law School are architectural gems. Don't miss the charming shops and art galleries that line the streets.
  • What are the best Airbnb and holiday rentals in Litchfield, CT?

    The Village Apt, Perfect - Peaceful Retreat and Cozy Litchfield House With Fenced-in Yard And Fire Pit are the most popular Airbnb and holiday rentals in Litchfield, CT among travellers.

  • Are there any unique natural phenomena in Litchfield, Connecticut?

    While Litchfield doesn't have dramatic natural phenomena like geysers, its rolling hills and forests offer a tranquil and scenic environment. The Bantam Lake, the largest natural lake entirely within Connecticut, provides opportunities for boating, fishing, and enjoying the natural beauty. Several hiking trails in the surrounding areas offer scenic views and a connection with nature.
  • What are the most popular Airbnbs in Litchfield, CT?

    Among the Airbnbs in Litchfield, CT, The Village Apt, Perfect - Peaceful Retreat and Artist's Garden Apartment are the most popular ones.

  • What essentials should you bring along for a trip to Litchfield, Connecticut?

    Pack comfortable walking shoes, as you'll be doing a lot of exploring on foot. Depending on the season, bring layers of clothing, as the weather can be unpredictable. Sunscreen, a hat, and insect repellent are also advisable, especially during warmer months. Don't forget a camera to capture the beautiful scenery and charming architecture.
  • What are the best holiday rentals with a pool in Litchfield, CT?

  • What famous events or festivals are happening in Litchfield, Connecticut?

    Litchfield hosts various smaller, local events throughout the year. Information on specific dates and events is best found closer to your travel dates by checking local event listings. However, the town's charm lies in its peaceful atmosphere and quaint celebrations rather than large-scale festivals.
  • What are the best rentals for families and kids in Litchfield, CT?

    The best rentals for families and kids in Litchfield, CT are Artist's Garden Apartment, County Seat Colonial and Center Of Litchfield House - Walk To Town.

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Litchfield, Connecticut?

    A daily budget in Litchfield can vary greatly depending on your preferences. Accommodation ranges from budget-friendly inns to more luxurious options. Food costs can range from casual dining to upscale restaurants. Transportation within Litchfield is often walkable, but a car might be needed for exploring the surrounding areas. A reasonable daily budget could range from £100 to £300 per person, but this is just an estimate.
  • What are the best rentals or Airbnbs with a jacuzzi in Litchfield, CT?

    The best holiday rentals or Airbnb with a jacuzzi in Litchfield, CT are 1770 Colonial 5 Bedrooms 4 1\/2 Baths Sleeps 9, Fantastic Cape In Historic Litchfield and Estate Guest House With Views.

  • Where can you find the best restaurants serving local dishes in Litchfield, Connecticut, and what are the must-try specialties?

    Litchfield has several excellent restaurants. The Village Restaurant is a popular choice known for its New England cuisine. For a more casual setting, try the West Street Grill. While there aren't specific 'local' dishes unique only to Litchfield, you can expect fresh, seasonal New England fare featuring seafood, locally sourced produce, and classic American comfort food.
  • What are some less-famous attractions in Litchfield, Connecticut that are worth a visit?

    The White Memorial Conservation Center offers beautiful trails and opportunities for wildlife viewing. The Bantam River, running through town, offers picturesque walks along its banks. Exploring the various antique shops scattered throughout the town can be a rewarding experience for those interested in history and unique finds.
  • What are the best activities for engaging with locals and understanding their culture in Litchfield, Connecticut?

    Strolling through the Litchfield Green and chatting with people you encounter is a great way to connect with the community. Visiting the local shops and art galleries allows for interaction with local artists and business owners. Attending any smaller community events or farmers' markets can also provide opportunities to meet locals and experience the town's culture.
  • What unique natural landscapes and terrain features can travellers explore in and around Litchfield, Connecticut?

    Litchfield's landscape is characterised by rolling hills, forests, and the Bantam Lake. The surrounding areas offer hiking trails with varying difficulty levels, providing opportunities to explore diverse natural landscapes. The lake itself provides stunning views and recreational opportunities.
  • How many days are ideal for a visit to Litchfield, Connecticut, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Litchfield and its surrounding areas. A possible itinerary could include exploring the Litchfield Green and historical sites on day one, visiting Bantam Lake and hiking trails on day two, and perhaps exploring nearby towns or engaging in some shopping on day three. This is just a suggestion; adjust it to your interests.

Nearby regions

Best Litchfield, CT holiday rentals with a sauna

Swiss Chalet On 16 Private Acres In Litchfield, Ct - Litchfield, CT
10 13 reviews

Swiss Chalet On 16 Private Acres In Litchfield, Ct

house, Watertown
This luxurious 5,100 sq ft Swiss-style lodge is situated in the Litchfield Hills, a 16-hectare estate approximately 16km from Litchfield and Washington, offering easy access to Black Rock State Park.
The property boasts four bedrooms, three bathrooms, sleeping up to ten guests, and features a heated swimming pool, jacuzzi, sauna, games room, and a fully equipped chef's kitchen; free horseback riding or a sailboat cruise are included with four-night-plus bookings.
Tranquil Home 10 Mins From Mohawk Mountain: Skiing, Hiking, Nature! - Litchfield, CT
10 1 review

Tranquil Home 10 Mins From Mohawk Mountain: Skiing, Hiking, Nature!

apartment, Litchfield
This modern riverside flat offers a secluded escape on 14 acres, located just a 5-minute drive from the amenities of Downtown Litchfield.
This 4-bedroom, 3-bathroom dwelling accommodates up to 8 guests and features a chef's kitchen, infrared sauna, and direct river access, with Bantam Lake, Mohawk Mountain, and local wineries all within easy reach.
Cozy Guest House On 15 Acres - Litchfield, CT
9.9 48 reviews

Cozy Guest House On 15 Acres

house, Litchfield
This Litchfield County guest house, situated on a secluded 15-acre plot, is minutes (approx. 2.4km) from Bantam Lake and Lake Waramaug, offering easy access to the Mohawk Ski Area and Litchfield's restaurants.
The two-bedroom property sleeps six, boasting a kitchen with fridge, freezer, and dishwasher, a garden, parking, air conditioning, Wi-Fi, and a bumper pool table; outdoor amenities include a patio and fire pit.
Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust - Litchfield, CT
9.6 21 reviews

Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust

apartment, Watertown
This charming house is located in a peaceful rural setting just six miles from Black Rock State Park, Bellamy-Ferriday House and Garden, and The Christmas Shop. It has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay.
This spacious residence spans 502 square metres and comfortably accommodates up to 12 guests in its four bedrooms and four bathrooms. You'll enjoy a range of amenities, including a private pool and spa, a fitness centre, a sauna, a tennis court, and a fully equipped kitchen.

Best Litchfield, CT holiday rentals with a fireplace

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm - Litchfield, CT
9.3 3 reviews

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

apartment, Torrington
This Torrington flat is located 22 kilometres from the Witch's Dungeon Classic Movie Museum and 26 kilometres from the Abbey of Regina Laudis.
This 74 square metre apartment offers private first-floor access, a cosy cabin-style interior, a fully equipped kitchen with an oven and washing machine, air conditioning, a fireplace, a balcony, and garden access, accommodating up to two guests.
Entire Litchfield County Lake House With Views - Litchfield, CT
10 16 reviews

Entire Litchfield County Lake House With Views

apartment, Morris
This spacious house sits above Bantam Lake in Litchfield Center, offering stunning views and easy access to the charming town's amenities and attractions, just 100 kilometers from New York City. The property enjoys excellent ratings for location, cleanliness and user experience.
The house has one bedroom and three bathrooms, comfortably accommodating up to eight guests. It features a well-equipped kitchen, a games room with a pool table and a master suite with a jacuzzi tub, and guests can enjoy the surrounding area's many outdoor activities, including fishing, swimming, and hiking.
Cozy Cabin Style Apt Private 1st Flr 1 Bdrm - Litchfield, CT
No reviews

Cozy Cabin Style Apt Private 1st Flr 1 Bdrm

apartment, Torrington
This apartment in Torrington, CT, is situated less than 1.6 kilometres from the historic downtown area, offering convenient access to the Warner Theatre and the Litchfield Historical Society Museum.
This 74 square metre, one-bedroom flat accommodates two guests and features a kitchen with a fridge, air conditioning, a terrace or balcony, garden access, and parking, making it suitable for families, business travellers, and ski trip enthusiasts.
Gracious Country Farmhouse - Litchfield, CT
10 6 reviews

Gracious Country Farmhouse

apartment, Litchfield
This secluded country house in Litchfield offers a peaceful wooded setting, yet is situated just 1.6 kilometres from Litchfield town green, providing convenient access to White Memorial park, local restaurants, and hiking trails.
This 4-bedroom, 2-bathroom property accommodates up to 8 guests and features a fully equipped kitchen, a basement pool table for entertainment, and is located 322 kilometres from both London and Paris.
©2026 cozycozy.com