Beachfront holiday rental in Chatham

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Popular amenities for Chatham beachfront rentals

Pet-friendly beachfront home rentals

Guest favourite
Home in Coxsackie
4.98 out of 5 average rating, 57 reviews

Hudson Riverfront home w/ private beach

NicholasRating, 5 stars2 months ago
We stayed here several times and it never disappoints. The property and house is peaceful and private. Yung and Nevin are so kind and very communicative. Always a great stay with plenty to see and eat in the area. We look forward to coming back.
Cottage in Hudson
4.82 out of 5 average rating, 132 reviews

Peaceful waterfront getaway (5 mi from Hudson, NY)

AshleyRating, 5 stars3 weeks ago
This was our second time staying at Tom’s beautiful property and once again it didn’t disappoint! Great place to relax and catch some fish by the fire. It was clean and comfortable. Lots of wildlife to see; bald eagles, turtles and even a beaver who would show up daily! Tom left us some fresh chicken and quail eggs in the fridge which were delicious. The location is quiet and peaceful but close enough to stores to grab essentials easily. Can’t wait to stay again next year!
Home in Niverville

Lakefront bungalow – your cozy escape

AmandaRating, 5 stars2 weeks ago
My family and I really enjoyed our stay. The house is super quaint and homey. It was a perfect spot to hang with family and relax. Everything was clean and comfortable. Mary Beth was a great host and quickly responded to any questions we had. If you don’t mind the train, this little lake cottage is the perfect spot. We loved listening to the birds and kayaking in the lake. The back porch felt like the main living room and after a run, the outside shower, with hot water, was a treat! I loved staying here, as did my family and we would stay again!
Superhost
Home in Monterey
4.82 out of 5 average rating, 79 reviews

Rustic 3bd Lake Front Country Cottage

EdwardRating, 5 stars4 weeks ago
Peaceful, perfect getaway. Jaryn’s cabin on Lake Garfield was the ideal escape—cozy, quiet, and surrounded by nature. We loved the lake access, morning coffee on the porch, and how easy everything was.
Superhost
Tent in Red Hook
5 out of 5 average rating, 7 reviews

Luxurious riverside glamping tent two

JoanaRating, 5 stars23 months ago
We had a very nice stay at Samuel and Catherine's little paradise in the nature. A large and clean tent with big double bed. The perfect escape from the city life - but not completely either because you have perfect wifi. A dip in the rivier gives nice refreshments. In the strong current you can play with their tubes bungee installation. Our hosts were very helpful and so friendly! They provided us with everything needed - even though it was not included. Bring good mosquito repellent ;)
Top Guest favourite
Apartment in Otis
4.96 out of 5 average rating, 96 reviews

Enjoy every season the Berkshires have to offer.

MarieRating, 5 stars1 week ago
We had a lovely relaxing time. The place was in a quiet, beautiful spot. Denise’s instructions were helpful and she was very welcoming. The place was spotless and the bed was extremely comfortable. We’d happily stay there again.
Superhost
Home in Rosendale
4.76 out of 5 average rating, 37 reviews

Luxury Retreat on Rondout Creek- Wedding Central!

DianeRating, 5 stars2 months ago
We were in Rosendale for a family funeral. The location was perfect and the accommodations perfect for our family. Thank you Travis for quickly responding to all my inquiries.
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 😊

Beachfront home rentals with a pool

Guest favourite
Home in Athens
4.94 out of 5 average rating, 67 reviews

Modern-Chic Athens Home - Fish, Ski & Swim!

NataliiaRating, 5 stars3 months ago
Thank you so much for your cozy and very comfortable house. Our vacation was perfect. We have already left your place. We will recommend your vacation home to everyone
Top Guest favourite
Home in Athens
5 out of 5 average rating, 58 reviews

5 BR Lakefront House w/ Hot Tub - Catskills

NehaRating, 5 stars7 months ago
We had a great time. We were able to kayak and use the other amenities on the property. Everything was well thought out. Scott was very communicative and responsive.
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!
Cabin in Austerlitz

The Cosmo Cottage

BrianRating, 5 stars2 days ago
look forward to renting again 4 sure
Farm stay in Accord
4.65 out of 5 average rating, 23 reviews

Family Farms Hudson Valley Estate

NadjaRating, 5 stars3 weeks ago
We had a great reunion weekend (4 adults) and were very comfortable at the farmhouse. Check-in was easy and we were greeted with farm fresh eggs in the kitchen. The house was spacious and un-fussy. The hot tub was fun and there were multiple common areas including sunroom & screened porch for spreading out and relaxing. The hot water was fabulous - all four of us were able to shower with no issues of water running cold. The grounds are pretty and private, lilacs were blooming, and all the animals were very sweet. There is a convenience store very close by which is handy and not typical in the countryside. The pool was not open when we were there but it was also very cold for May. Bethany was a fantastic host - responsive, friendly and generous - we had a wonderful stay.

Private beachfront home rentals

Home in Pine Plains
4.77 out of 5 average rating, 97 reviews

Designer Lakefront house, a hiking-ski retreat.

DanielRating, 5 stars1 month ago
Convenient location, easy to get into and a beautiful view of the lake!
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.
Guesthouse in Rhinebeck
4.86 out of 5 average rating, 66 reviews

Enjoy life on a lake, 90 mn from NYC privacy

DavidRating, 5 stars7 months ago
Great experience throughout our stay. We loved the beautiful surroundings. Having coffee in the morning out on the dock by the pond was a personal favorite. Highly recommend Sarah's place for a visit and a peaceful and relaxing stay.
Guest favourite
Home in Becket
4.96 out of 5 average rating, 26 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars5 months ago
We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).
Guest favourite
Home in Palenville
4.97 out of 5 average rating, 38 reviews

Giant Serene Private Luxury Creekside Home

MegumiRating, 5 stars1 week ago
We had a great time staying at Lea and Jeff’s place. Quiet and safe. Enjoyed watching hummingbirds everyday. Lea was an amazing host, welcoming, and flexible, made sure we were comfortable staying at her house. Thank you!
Top Guest favourite
Home in Tolland
5 out of 5 average rating, 33 reviews

Lakefront Retreat at Porcupine Place

BrianaRating, 5 stars1 week ago
This place was beautiful and very peaceful. The neighborhood is super quiet. It was a great place to stay and wake up in the morning and drink my morning coffee while listening to nature and look out at cranberry pond. Unfortunately it was a very busy weekend due to staying here for a wedding so I did not get to fully enjoy this cute place that included a paddle boat, fire pit and kayaks. I would definitely recommend this quiet get away to anyone looking for a peaceful vacation or an outdoor vacation with the kids at the lake. The host was also super responsive and helpful during my stay. Only challenging thing that happened which might not happen for everyone is the address had me a couple campsites before the actual location (got to love technology and GPS right). We were able to find it once we drove a little bit farther. However this could have just been my GPS but wanted to give people the heads up if they are also in my position and coming during the nighttime.
Guest favourite
Home in Becket
4.94 out of 5 average rating, 31 reviews

Lakefront Cottage on Private Beach

GillianRating, 5 stars3 weeks ago
Our family had an AMAZING stay in this cottage. It was clean and comfortable, and just what we were looking for. A quiet spot where we could enjoy fishing, kayaking, biking, etc with the comforts of home. Because of all the amenities offered, we didn’t have to pack too much which is always a bonus! We are already talking about our next visit 😊
Top Guest favourite
Apartment in Chichester
4.93 out of 5 average rating, 152 reviews

STREAMSIDE CATSKILL MOUNTAIN HOUSE

TarikRating, 5 stars1 month ago
Ian’s place was magical. So quiet, cozy, clean and a great place to enjoy nature and surrounding country side. Close enough to town, restaurants and other destinations but still far enough to enjoy the countryside side. Ian was friendly, responsive and answered all our questions. He left clear instructions by the entrance and was easy to reach. We even got to meet him in person before we left. Highly recommend this place for anyone wanting to explore the Catskills and looking for a weekend getaway.

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