
Beachfront holiday rental in Litchfield County
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Top-rated beachfront accommodation in Litchfield County
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Popular amenities for Litchfield County beachfront rentals
Pet-friendly beachfront home rentals

Rustic 3bd Lake Front Country Cottage
Very rustic, private, peaceful kind of like a camp but with air conditioning and excellent wifi. Bald eagle sat over the lake outside. Kayaks were fun. Tons of great hikes and historical things to see. Town of Great Barrington and Sheffield have great antiquing both high and low end. I would go back any time.

Modern and Stylish Country Lakeside Cottage
This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!

Ridgeview Suite at Stony Creek Depot
Barbara’s place reminded me of the way airbnbs used to be. It felt like home-away-from-home. The accommodations were high quality and clean, and there were even some tasty snacks! We loved our stay. Everything was as pictured. Stony Creek was wonderful, and we look forward to visiting again next year!

Rustic Cabin+ Private Beach Pond, Stars & Wildlife
Amazing cabin!! My third visit. Was there with friends for fishing and I love the cabin so much that I booked my anniversary weekend and my wife is also in love with the property. Relaxing Birding Fishing Kayaking Fire pit Romantic This place has it all! Book it now! You won’t regret it!

Enjoy every season the Berkshires have to offer.
The space is very clean. I stayed 2 nights and brought my dog with me. The only thing that I was surprised about was that there wasn't a door to the bedroom area. I had looked at the pictures and assumed the door I saw was to the bedroom but it was a closet. The bed area is separated by a partial wall but not an actual door. Something to keep in mind if you have additional people sleeping on the pull out couch.

Artsy lake house on an island
We had a great time in Vladimir & Annie’s house. The house was clean & comfortable. The balcony of the lake’s view was amazing. We spent a fantastic time by having some morning breakfast on it and listening the birds songs… Special thanks for their flexibility with checking in & out. Highly recommended this house for our friends and family and looking forward to be back 😊

Private Lakefront Bungalow
Excellent little retreat! Highly recommend for a weekend away. Our recommendation is to arrive at the house before dark as there is a windy dirt road leading up - everything else was perfect!

A Beachfront Getaway
Great place for a long weekend. Plenty of spots within walking distance and the beach was perfect
Beachfront home rentals with a pool

Waterfalls and Trails at 'The Mills At Green Hole'
We held our Thanksgiving holiday at The Mills at Green Hole and we couldn't have been happier. The house comfortably fit our group of 13, with plenty of beds and nice large gathering spaces on the first floor. The property is full of character and has a such a cool and unique history. While the weather didn't cooperate for us this time around, the grounds are great for outdoor gatherings and the river / waterfall is quite unbelievable. We look forward to coming back again soon!

Private Luxury Waterfront Home
We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

Ocean Front Condo w/ Pool
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1 Bed Pond Cottage w/ Pool/Hot tub/Sauna access
Sarah's place is an absolute gem! From the beautiful views and serene atmosphere to the cozy cottage and amenities, our experience was truly special. While the weather didn't cooperate for us to use the pool, and the hot tub wasn’t available, we made the most of the sauna and spent time enjoying the rest of the property. The lake views and peaceful surroundings, made our stay unforgettable. Sarah, Anya, and the whole family were extremely welcoming and great hosts. They made sure we had everything we needed and were always quick to respond to any questions. The property offers everything you need for a relaxing getaway, and it’s conveniently close to Kent for some great outings to restaurants and shops We highly recommend this spot for anyone looking for a quiet retreat with nature and serenity. We’ll definitely be back!

New Haven Gem w/ Private Pool, Walk to Beach!
Our group of 6 has a great time at the home! The backyard is beautiful and has plenty of seating. We didn’t get to enjoy the pool because it was a bit chilly for May, but would be GREAT in the summer! Would definitely return!
Private beachfront home rentals

Beachfront Cottage Serene Private Beach, Kayaks
We loved it. Redefines “fully stocked” - David’s place had everything we could ask for. The water at high tide was magical. Kayaking, fishing and we found over 100 (literally) hermit crabs.

Scenic Mulberry Point Connecticut Beach House
Michael and Marchen's house is in a lovely location right next to a pretty little beach; the house is airy, light, and very comfortable, and the views of the water from outdoors (and indoors!) are great. We were there for a graduation weekend, so didn't spend a lot of time hanging out at the house, but we would have enjoyed doing that, too. Kitchen was well-equipped; bathroom was clean and modern and pretty; beds very comfortable! Marchen was very responsive and helpful--all in all, a lovely stay and we'd stay again.

The Jewel of The Cove - Historic Coastal Retreat
Edward made the stay easy and we were very comfortable. House is lovely and very very clean. Would stay at the house again!

Beautiful, Spacious, Waterfront Home on the Bay
Had a great stay over Christmas Holiday with family. House was big, convenient, clean and easy to get into. Great view of the ocean. Would definitely stay there again.

Cozy Cottage on the Lake
The cottage was easy to check into, clean, and very cozy. It was decorated for the holidays which was perfect for our weekend. We enjoyed the fireplace and the games in the cabin as well! I would consider coming back in the summer to enjoy the outdoor area and lake. Ann-Marie and Carl provided really helpful instructions on how to get to the house.

Berkshire Ski House on Lake Garfield W/HT By GB
This house was great for a winter weekend getaway! Great Barrington, Lenox, and Stockbridge are all adorable towns to visit and are a 15 - 30m drive away. The house itself was cozy and had all the amenities we needed. Shay was very responsive. Something to know about the area is that ride shares and cabs are hard to come by, so having a car that fit everyone we were traveling with was crucial for our group to get around town.

The Eagle- Private Beach
Great location with private beach access. Cozy 2-bedroom slept our family of 4 comfortably. Comfortable beds, great shower pressure, and large yard out back. I’m originally from Branford and we visit my parents regularly. Will definitely keep Abigail’s home in mind for future visits!

Coastal getaway with water views in every room
Meaghan’s place was everything we needed and more! Loved the views, the waves, the sea breeze, the bird observing, the walks to Grass Island, the together time with family in a quiet, secure & well appointed setting. Meaghan equipped us with everything! She was very responsive to answer questions. This is one of those treasured memories. Can’t wait until we get back again to this special location! Thank you!
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- Fairfield Beach
- Yale University
- Six Flags New England
- Walnut Public Beach
- TPC River Highlands
- Thunder Ridge Ski Area
- Woodmont Beach
- Jennings Beach
- Seaside Beach
- Silver Sands Beach
- Bushnell Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Calf Pasture Beach
- Kent Falls State Park
- Wildemere Beach
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Sherwood Island State Park
- Bayview Beach
- Hudson Highlands State Park
- Brownstone Adventure Sports Park
- Anchor Beach
- South Pine Creek Beach