
Pet-friendly vacation rentals in Litchfield
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Top-rated pet-friendly home rentals in Litchfield
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Popular amenities for Litchfield pet-friendly home rentals
Pet-friendly house rentals

Vacation Home In Millerton
If there were more stars this place would warrant them. Incredibly clean and thoughtfully stocked. The appliances were great, the cupboards were full of dishes, pots and pans. Bed linens were pristine. Very spacious and quiet. We were very happy here.

Private Hudson Valley Country Retreat
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back

Fantasy Cottage/Mountain Views/Trails/Fire pit
Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.

Luxe Bolton Lake
Super clean, quiet and comfortable with lots of great touches. We didn’t get the best weather for lake life but the house made up for it nicely. Look forward to staying again someday!

Romantic Getaway at The Lake!
We had an amazing stay! The location was amazing and the hot tub was perfect! Lots of fun activities to do in the area as well and Marissa gave so many great recommendations. My husband and I had a great time !

The Waterfall House
When you are accustom to five star and you just want a place to be absolutely quiet and be present with nature , this places is it !

The Gatehouse at Raspberry Ridge
Lawrence and Ilze are great hosts! They actually just live next to the house and they own a farm. We took our kid to visit their farms with lots of beautiful chickens and roosters. My son even has a chance to feed the chickens. We will definitely come back!

Granite Ledge, Modern home in a unique setting
This was our favorite Airbnb of the ones we've stayed at in New England over the years. The house is more spacious than it appeared on photos. The design of the space is minimalist and modern which we loved. Our favorite was grilling/having breakfast in the backyard that faces the giant rock - which is truly a special treat - and cooking in the spacious, well-stocked kitchen together. If we come back to the Berkshires we would love to stay at Benjamin's place again.
Pet-friendly home rentals with a pool

Charming Guest Cottage with Modern Amenities
This place is absolutely gorgeous. I spent quite a bit of time just exploring the grounds with my dog. It was too cold to use the pool but it was still beautiful to look at and a nice view while I was cooking/washing dishes. I appreciate the tour I received when I arrived to show me around. I would definitely recommend this place and hope to book again in the future.

The Granary at House on Golden Hill
We had a great stay. The apartment is peaceful and clean. I particularly loved the soaking tub! Jared was very responsive to all my questions and provided great coffee for the morning.

Pool House
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

The Creation Station
Very nice place, beautiful big deck, awesome creativity to the lighting around the property. A walking path, fire pit, hot tub, big deck to relax on, and a fully equipped stage. It is a step above camping but not quite glamping. A lot of fun, and Apple is a sweet bonus hostess.

Charming apartment with breathtaking view!
Patrick and Monica were incredibly welcoming, making us feel right at home. They were communicative, helpful, and especially great with our dogs. We loved the property and left feeling fully rested. We would love to come back!

Prvt pool Huge, Eclectic space… 1.5 hr to NYC!
Blake is a kind and attentive host. The house is fun and eclectic. Many interesting things to look at, art books to leaf through and she has a great record album collection. It has all the necessities you would hope to see in an airbandb. I like the location. We enjoyed taking a hike in Mount Beacon park to see the remnants of an old casino and great views of the Hudson Valley.

Modern Upstate Cabin, near Rhinebeck NY
We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Obsessed with this Airbnb! My husband, dog and I typically go to upstate NY or the Berkshires for long weekends but I came across this Airbnb as I had an event in westchester over the long weekend. Highly recommend! So much hiking, wonderful restaurants and so close to the city. My dog loved this property as well! Will be back.
Private, pet-friendly home rentals

The Inn at Knife Shop Falls- Historic Waterfront
Our getaway for the weekend was perfect! We enjoyed the home, pond and a nearby preserve for a hike. Thank you for the stay!

Cozy Scenic New England country retreat w/ hiking
This place is lovely. Has everything you need. Remarkably clean! They gave a lot of extras, like shampoo, conditioner, paper towels and a sponge. Very friendly attentive hosts and lots of privacy. The town of Sherman doesn't have much but a beautiful beach on the lake -- but 15 min away New Milford has artisinal and chain businesses. My only negative was with ticks. I brought 2 small dogs who are treated with preventative, but that doesn't stop ticks from crawling on them. My first few minutes outside in the grass and on the deck resulted in multiple ticks on them. They then tracked them inside bc I saw several in the unit. Andy gave me advice which was nice and Kim told me that it's just a matter of if deer were just on the property. This is no fault of their own - but maybe a heads up would be nice to other dog owners that you will be battling ticks during your stay. on the last night a tick crawled across my laptop in bed. It was stressful to constantly check my dogs and myself.

Private and Serene home close to I-84 and shopping
As advertised. Perfect location for what we needed. Perfect two people. Tighter for three. It got cramped with four. Saverio was an excellent host-very responsive. If anything was needed (toilet paper, garbage bags, etc) he was able to provide very quickly. The site is a hikers paradise with access to town trails from the property.

Private Woodland Sanctuary—3 mins to a lake beach!
this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.

The Ancram A - Luxury Mid-Century Modern Cabin
We had a fantastic weekend celebrating my wife’s birthday here. The home is beautiful, peaceful, and surrounded by nature—just what we needed. Everything was clean, comfortable, and thoughtfully set up. We’d love to come back!

Charming Home in Litchfield County on a MAIN ROAD!
Perfect placement, central to our needs. I love the fact my dog didn't have to be in a crate while we were out. I also love that there were laundry and dishwasher pods. Fantastic stay overall.

The House on the Hill
Ina’s home, on 48 acres, is consistently highly rated, as it should be. It’s a perfect retreat for 2-3 people, secluded, but only a short drive to Litchfield. Ina kindly met us to give a 10 min tour of the property. Although not huge, the house is a congenial, inviting space, which was beautifully designed/built in the 50’s and sympathetically incorporates architectural components from a much earlier period. The setting, with several areas to sit out in, affords peace and spectacular sunsets. All said, this is a unique, magical space.

Peaceful Barn Retreat
We had a beautiful stay at this barn! Lots of space and a large/comfy bed. Definitely will stay here again in the future! There is a little town down the road with lots of dining options. A lot of trails for hiking/walking around the area!
Quick stats about vacation rentals that are pet-friendly in Litchfield
Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ404 before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
40 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Fairfield Beach
- Yale University
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Seaside Beach
- Bushnell Park
- Calf Pasture Beach
- Jennings Beach
- Silver Sands Beach
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Walkway Over the Hudson State Historic Park
- Clinton Town Beach
- Sherwood Island State Park
- Bayview Beach
- Grove Beach
- Hudson Highlands State Park
- Kent Falls State Park
- Wildemere Beach
- South Pine Creek Beach