Beachfront holiday rental in Litchfield County

Find and book unique beachfront homes on Airbnb

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Popular amenities for Litchfield County beachfront rentals

Pet-friendly beachfront home rentals

Superhost
Home in Monterey
4.83 out of 5 average rating, 80 reviews

Rustic 3bd Lake Front Country Cottage

SarahRating, 5 stars5 days ago
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.
Guest favourite
Home in Egremont
4.91 out of 5 average rating, 82 reviews

Modern and Stylish Country Lakeside Cottage

NikiRating, 5 stars3 weeks ago
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!
Guest favourite
Apartment in Branford
4.97 out of 5 average rating, 107 reviews

Ridgeview Suite at Stony Creek Depot

EmilyRating, 5 stars2 weeks ago
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!
Guest favourite
Cabin in Colebrook
4.94 out of 5 average rating, 95 reviews

Rustic Cabin+ Private Beach Pond, Stars & Wildlife

EdwardRating, 5 stars2 weeks ago
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!
Top Guest favourite
Apartment in Otis
4.96 out of 5 average rating, 97 reviews

Enjoy every season the Berkshires have to offer.

MicheleRating, 5 stars3 days ago
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.
Guest favourite
Home in Copake
4.93 out of 5 average rating, 29 reviews

Artsy lake house on an island

EamonRating, 5 stars3 weeks ago
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 😊
Superhost
Home in Rhinebeck
4.82 out of 5 average rating, 272 reviews

Private Lakefront Bungalow

NickRating, 5 stars3 weeks ago
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!
Guest favourite
Cottage in West Haven
4.91 out of 5 average rating, 35 reviews

A Beachfront Getaway

JamesRating, 5 stars1 month ago
Great place for a long weekend. Plenty of spots within walking distance and the beach was perfect

Beachfront home rentals with a pool

Guest favourite
Home in Hillsdale
5 out of 5 average rating, 43 reviews

Waterfalls and Trails at 'The Mills At Green Hole'

DanRating, 5 stars6 months ago
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!
Superhost
Villa in Guilford
4.91 out of 5 average rating, 11 reviews

Private Luxury Waterfront Home

VirginiaRating, 5 stars22 months ago
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.
Private room in West Haven

Ocean Front Condo w/ Pool

MaxenceRating, 5 stars8 months ago
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Guest favourite
Cottage in Kent
4.88 out of 5 average rating, 85 reviews

1 Bed Pond Cottage w/ Pool/Hot tub/Sauna access

LucyRating, 5 stars3 weeks ago
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!
Home in New Haven
4.59 out of 5 average rating, 22 reviews

New Haven Gem w/ Private Pool, Walk to Beach!

MarloRating, 5 stars3 weeks ago
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

Guest favourite
Cottage in Branford
5 out of 5 average rating, 10 reviews

Beachfront Cottage Serene Private Beach, Kayaks

BasilRating, 5 stars9 months ago
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.
Guest favourite
Home in Guilford
4.94 out of 5 average rating, 70 reviews

Scenic Mulberry Point Connecticut Beach House

AndreaRating, 5 stars1 month ago
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.
Superhost
Home in New Haven
5 out of 5 average rating, 14 reviews

The Jewel of The Cove - Historic Coastal Retreat

DaraRating, 5 stars1 month ago
Edward made the stay easy and we were very comfortable. House is lovely and very very clean. Would stay at the house again!
Guest favourite
Home in West Haven
4.97 out of 5 average rating, 29 reviews

Beautiful, Spacious, Waterfront Home on the Bay

KevinRating, 5 stars5 months ago
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.
Guest favourite
Cottage in Becket
4.81 out of 5 average rating, 54 reviews

Cozy Cottage on the Lake

PaigeRating, 5 stars5 months ago
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.
Superhost
Home in Monterey
4.88 out of 5 average rating, 8 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

MaryRating, 5 stars4 months ago
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.
Top Guest favourite
Home in Branford
4.98 out of 5 average rating, 40 reviews

The Eagle- Private Beach

StephanieRating, 5 stars3 weeks ago
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!
Superhost
Home in Madison
4.89 out of 5 average rating, 45 reviews

Coastal getaway with water views in every room

KathyRating, 5 stars10 months ago
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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