
Family-friendly vacation rentals in Litchfield County
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Top-rated family-friendly rentals in Litchfield County
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Popular amenities for Litchfield County family-friendly rentals
Family-friendly home rentals with a hot tub

ZoomIn Map BestTown Washington "Kirby" PoshPadsCT
Beautiful house, gorgeous and convenient location, excellent host. We had a great stay.

Home in historic Litchfield village
Jeannine’s home was an absolute gem! We had our annual girls weekend here and felt right at home. The house was so cozy and warm yet had ample space for me and the girls to sit and chat together. We loved that the house was lived in with family photos and mementos around, rather than being sterile like many other bnbs we’ve stayed in. There was also so much to do in the surrounding area! I would definitely recommend this stay :)

Charming farmhouse retreat with post-hike hot-tub
Very responsive host. The house was exactly as described and pictured. Easy to understand instructions for check in and check out.

1700 Historical Home on 26 Acres Near Schools
The house is beautiful with lots of amenities. The kitchen was nice and big for cooking. We spent a lot if time in the library using the fireplace. The surround sound speaker system was great for listening to music. DeeAnne stays in an attached apartment, but with it’s own entrance/exit. She was not in our way at all during the stay. This house was perfect for our group of 10.

Prana Residence Spa with Indoor Pool (near Kent)
Prana is a cozy, relaxing retreat. Our family had a great time warming ourselves around the fireplace, relaxing in the hot tub, and snoozing in the sauna. It was a great post-Christmas getaway!

Glorious Washington Country Estate
This was a beautiful, historic home. The pool/ spa area was perfect for the 8 of us. We spent days lounging in the pool, visiting wineries, Kent, Kent Falls, New Preston and touring the area. We also spent time on the hiking trails that are accessible right from the property. The little town of Washington was quaint and had the basics of what you may need. A Wonderful book store and coffee shop (Marty’s Cafe, their gluten free pastries were fantastic). There was even a small market. We would definitely recommend the G W Tavern for dinner. Gregory was very easy to communicate with and answered all our questions and concerns. Having a full time automatic generator was really wonderful, we had some storms while we were there and the neighbors were without power but we continued on without interruption. Even the house A/C, spa and pool filter and heater were up and running. Our daily visits from all the wildlife and resident spirit were magical. We loved our time here!
Family- and pet-friendly home rentals

The 1913 House, book 6 days get the 7th free.
We had a fantastic 2-night stay at Jim’s beautiful old home. So clean, so thoughtful & tasteful decorated. Great first sunny day for biking & hiking on Harlem Valley Rail Trail and close to restaurants in town. But also great second day when caught in snowstorm. Jim’s house is warm, cozy, comfortable, perfect for a day to relax, read, watch movies, cook, and enjoy the beautiful view. Thank you and we will certainly come back.

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Sweet Dotties Cottage was better than expected. It was right on the water and even had a dock for our boat. It was very clean and exactly as described. The screened in porch was great at night. I highly recommend and will be visiting this property again.

Candlewood Lakehouse Home, Private Dock, Kayaks
My reservation at another property was mysteriously cancelled 3 days before my family's wedding. After 24 hours of back and forth with Airbnb, Mary saved the day and worked with myself and airbnb to get me rebooked into her amazing family home. She was an angel!

Carriage House in two acres of Eden
Wonderful place to stay, this was our home base for a Christmas visit with family and it was a great and cozy spot to come home to each night. Beautiful back yard!

Rural Litchfield County Apartment Goshen CT
Studio apartment was what we needed for a weekend of skiing - close to Mohawk Mt, clean, and at a reasonable price. There was a little kitchenette area with microwave, k cup machine and refrigerator. The heat was very responsive and kept the place toasty. Scenery of the adjacent farm was very nice. Would recommend

The House on the Hill
We've stayed several times over the past year or so--Ina's cottage is our favorite weekend getaway from the city. The setting is just right--you can see the sunrise and sunset from its hilltop location, which offers lovely views across the surrounding countryside. Last weekend, we watched bluebirds feeding in the meadows nearby. Inside, the cottage is charming and filled with characterful furnishings and decor. All is immaculate and thoughtfully equipped from kitchen to bathrooms for a comfortable stay. We love the privacy that Ina's space provides with options for good restaurants, swimming, and hiking nearby in surrounding towns. Ina, we loved the pumpkin and gourds in the cottage and thank you again for a delightful stay.

Kent village home 2 hrs from NYC
We had a wonderful stay at Niva's home in Kent. The house is beautifully decorated and perfectly clean. Niva's place is great-looking and very comfortable. It is just a short walk into the charming town of Kent, CT. Niva was a communicative and friendly host. Thank you, Niva!

Private 1 bedroom apartment in central Connecticut
I was very pleased at the pet- friendly features of this home away from home. There was lighting throughout the edge of the backyard which allowed me to safely take my dogs out before bedtime. We also took short walks in the neighborhood. The area was very quiet at night and I slept very well. I lived in the same city in a different area for years and had never experienced that level of quiet!
Family-friendly home rentals with a pool

Enchanted Cottage~Complete Privacy~Pool & EVC!
Absolutely beautiful location, amazing pool. Joseph was a responsive and helpful host. Great stay!

Fallen Fence 40 Private Acres Heated Pool & EVC!
We had a fabulous stay at Fallen Fence for my in-laws 50th anniversary weekend. The home is spacious and the property is stunning.

Scandinavian Modern Upstate House w/Pool & Sauna
The most beautiful home and view. The most gracious host. We couldn’t have asked for more!

A Yard in the Country
This is a home not a rental and as such it is fully equipped to say the least. It included: - Utensils for cooking, eating, drinking for large amounts of people - Alcohol, soft drinks, mixers found in 3! refrigerators in addition to the bar - Coffee, both ground & single serve that lasted the whole week - Sports stuff, you name the sport and there’s equipment already there - Comprehensive House manual, our only problem was not referring to it immediately There’s also a wonderful deck, great room and grounds as advertised not to mention pool, pool house and barbecue. Would highly recommend and would book again although more likely in the summer where we could use all of the features offered.

BUNTING HOUSE : CANDLEWOOD LAKEFRONT! 3BR CHALET
The place and location are gorgeous. Right on the lake with a private dock. The host is super nice and responsive. I couldn’t ask for a better experience.
Destinations to explore
- Rentals with breakfast Litchfield County
- Waterfront rentals Litchfield County
- Rentals with pools Litchfield County
- Rentals with outdoor seating Litchfield County
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- Beachfront rentals Litchfield County
- House rentals Litchfield County
- Rentals with a washer and dryer Litchfield County
- Rentals with a patio Litchfield County
- Rentals with lake access Litchfield County
- Kid-friendly rentals Litchfield County
- Rentals with a kayak Litchfield County
- Bed and breakfasts Litchfield County
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- Rentals with a fireplace Litchfield County
- Rentals with a hot tub Litchfield County
- Pet-friendly rentals Litchfield County
- Cottage rentals Litchfield County
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- Rentals with a fire pit Litchfield County
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- Yale University
- Catamount Mountain Ski Resort
- Thunder Ridge Ski Area
- Six Flags New England
- Taconic State Park
- Woodmont Beach
- Marvin Beach
- Bousquet Mountain Ski Area
- South Pine Creek Beach
- Wildemere Beach
- Morningside Beach
- Anchor Beach
- Sasco Hill Beach
- Mohawk Mountain Ski Area
- Opus 40
- Beartown State Forest
- Thaddeus Hait Farm
- Kent Falls State Park
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Wee Burn Country Club Inc
- The Stanwich Club
- Woodway Country Club
- Bull's Bridge Golf Club