Beachfront vacation rentals in Chatham

Find and book unique beachfront homes on Airbnb

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Popular amenities for Chatham beachfront rentals

Pet-friendly beachfront home rentals

Superhost
Home in Monterey
4.81 out of 5 average rating, 75 reviews

Rustic 3bd Lake Front Country Cottage

ChristopherRating, 5 stars5 days ago
We thoroughly enjoyed our stay at this property—it was truly a delightful experience. The setting is serene, with beautiful views that made our time there feel peaceful and restorative. The house itself is exceptionally clean and full of character. We particularly appreciated the eclectic wall hangings throughout, which added a unique and personal touch to the space. The furniture was comfortable and evoked a charming 1970s vibe that we found both nostalgic and inviting. The kitchen is modern and well-equipped with everything one might need, making meal preparation easy and enjoyable. The beds and bedding were also very comfortable, ensuring a restful night's sleep. One of the true highlights was the abundance of outdoor space, which provided plenty of room to relax, gather, and take in the natural surroundings. All in all, this home was a real treat, and we’re grateful to have had the opportunity to stay here.
Guest favorite
Home in Wingdale
4.94 out of 5 average rating, 16 reviews

Your own private lake + beach, boats & game room!

BlairRating, 5 stars4 months ago
John & Laurie’s home was warm and inviting for our group’s New Years holiday. We were welcomed with a lovely bottle of wine and a well stocked kitchen. We weren’t able to make use of the lake because it was January but enjoyed walks around the property and the incredible bird sightings ! Bedrooms were cozy and the home is clean and well sized for a big group. Thanks so much !
Guest favorite
Home in Egremont
4.94 out of 5 average rating, 78 reviews

Modern and Stylish Country Lakeside Cottage

SeanRating, 5 stars3 days ago
Hello - Great to be back in Maureen's home. Super excellent location 5mins or so to Great Barrington and close to everything the Berkshires has to offer. Home is really amazing for a romantic weekend away, my partner and I both loved everything about the home and the surrounding property. no notes.
Superhost
Tent in Red Hook
5 out of 5 average rating, 7 reviews

Luxurious riverside glamping tent two

JoanaRating, 5 stars22 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 ;)
Guest favorite
Cabin in Colebrook
4.93 out of 5 average rating, 92 reviews

Cozy rustic cabin with beach on pond with 7 acres!

Prafful SinghRating, 5 stars2 months ago
We really enjoyed our stay at the cabin. Our pets loved taking long naps by the fireplace. - clean place - responsive host - private and peaceful
Guest favorite
Cottage in Ulster Park
4.91 out of 5 average rating, 180 reviews

Romantic House on a Magical Lake

VidhiRating, 5 stars1 month ago
Comfortable and clean with beautiful scenery - on clear days, you get a Mountain view across the lake! Highly recommend.
Guest favorite
Home in Becket
4.96 out of 5 average rating, 70 reviews

Berkshires Retreat W/ Sauna by Evergreen Home

JanieRating, 5 stars1 month ago
Private, secluded and cozy weekend away. The space was just as described and more private than expected. We loved waking up with the daylight and relaxing at night with the open sky and sauna sessions. Area recommendations were spot on and made the trip even more enjoyable. Hope to be able to get back during a different season to enjoy the area again!
Guest favorite
Apartment in Otis
4.96 out of 5 average rating, 92 reviews

Enjoy every season the Berkshires have to offer.

AndreaRating, 5 stars2 months ago
Extremely clean and peaceful place. Very cute and cozy set up as well! Denise and John are excellent hosts. Upon leaving, our car unfortunately got stuck a mile out from the house in some deep snow. John saved the day and immediately came to the rescue to tow us out. His kindness and quick response saved me a lot of stress. Highly recommend John and Denise for their exceptional hospitality and willingness to go the extra mile!

Beachfront home rentals with a pool

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

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

NataliiaRating, 5 stars2 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 favorite
Home in Athens
5 out of 5 average rating, 57 reviews

5 BR Lakefront House w/ Hot Tub - Catskills

MickeyRating, 5 stars6 months ago
Can’t recommend this airbnb strong enough. The location is absolutely perfect, and Scott was the most responsive and helpful host I’ve had in my many years using airbnb. I’ll definitely return
Guest favorite
Cabin in Ellenville
4.93 out of 5 average rating, 68 reviews

Secluded Luxury Lodge w HotTub & Fireplace

SimoneRating, 5 stars3 days ago
Linsey’s home was a beautiful setting for a girls weekend. It was cozy, had plenty of comfortable beds and amenities. The only thing to be aware of is that the basement is very cold (or at least while we were there), so perhaps being prepared with warm clothing if you spend time down there!
Guest favorite
Home in Hillsdale
5 out of 5 average rating, 43 reviews

Waterfalls and Trails at 'The Mills At Green Hole'

DanRating, 5 stars5 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!
Top guest favorite
Villa in Athens
4.98 out of 5 average rating, 46 reviews

Hudson River Estate with salt.water infinity pool

EmilyRating, 5 stars4 months ago
This house is gorgeous!! Our group had a fantastic time. There is so much space, plenty of room for the three families we had staying there. All the kids loved it at Jean's house, from the babies to the 5 year old there was plenty to do and lots of amenities. The theater room was a huge hit! The hot tub was perfect for the adults and we loved how close it was to the house so we could run in after getting out! The view was fantastic even in the winter. We are already talking about coming back in the summer to enjoy the gorgeous infinity pool. This place is really special and we will be talking about it for a long time.
Farm stay in Accord
4.58 out of 5 average rating, 19 reviews

Family Farms Hudson Valley Estate

KristenRating, 5 stars3 weeks ago
We had an incredible experience at Bethany’s farmhouse. Bethany was so easy to communicate with and she was so thoughtful to get us a bottle of wine and leave farm fresh eggs for us to enjoy. The farmhouse was quiet and secluded, but not too far from Mohonk Mountain House and the town of New Paltz. We all slept like babies, enjoyed soaking in the hot tub, exploring the surrounding woods, and tending to some spring chicks! If you are looking for some serenity in the “Gunks”, I highly recommend Bethany’s farmhouse for your stay.
Guest favorite
Cottage in Kent
4.88 out of 5 average rating, 83 reviews

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

TeadoraRating, 5 stars2 months ago
The home was spotless and the view was even better than the photos. The living room has tons of windows and great fireplace.

Private beachfront home rentals

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

Hudson Riverfront home w/ private beach

NicholasRating, 5 stars1 month 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.
Home in Pine Plains
4.77 out of 5 average rating, 95 reviews

Designer Lakefront house, a hiking-ski retreat.

ElizabethRating, 5 stars2 weeks ago
Thank you Joanna, the Missoula Children's Theater instructors loved your place and wanted to move in!
Cottage in Hudson
4.82 out of 5 average rating, 131 reviews

Peaceful waterfront getaway (5 mi from Hudson, NY)

TaylorRating, 5 stars3 months ago
Tom’s place was exactly as described! All descriptions and directions provided were amazingly helpful and accurate. This place was perfect for a weekend getaway for me and my dog. Another great part was the farm visit! Kathy and Tom were super friendly in showing me all the animals. I would definitely recommend this place and am looking forward to potentially visiting again in the summer!
Guest favorite
Cottage in Becket
4.81 out of 5 average rating, 53 reviews

Cozy Cottage on the Lake

PaigeRating, 5 stars4 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.
Guest favorite
Home in Becket
4.96 out of 5 average rating, 25 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars4 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).
Top guest favorite
Home in Tolland
5 out of 5 average rating, 31 reviews

Lakefront Retreat at Porcupine Place

LaurieRating, 5 stars1 month ago
Obsessed! if a house could be a soul mate I met mine! I don't say that lightly, I am everything real estate, holding, buying, selling, air bnbs, construction, sales and staging.......and this house could not have been any better. Cherishing the old, while putting new where needed. Let's you feel like you are at the lake without one thing on the to do list. Trees and water, seclusion without being alone. Everything in a logical, well thought out position. The experience from tennis to childlike wondering in the woods, with the most accommodating host that didn't overly reach out. I will be back for all of my peaceful getaways with my daughter. So very grateful for what this host offered us.
Guest favorite
Home in Becket
4.93 out of 5 average rating, 29 reviews

Lakefront Cottage on Private Beach

DaveRating, 5 stars5 months ago
Daphne is a thoughtful and wonderful host. The property was clean, comfortable and very well appointed with everything I would need, especially in the kitchen. I highly recommend this 5-star property. It is quiet, peaceful and full of nature everywhere the eye can see.
Top guest favorite
Apartment in Chichester
4.93 out of 5 average rating, 151 reviews

STREAMSIDE CATSKILL MOUNTAIN HOUSE

JohnRating, 5 stars2 months ago
Great weekend in the Catskills - Ian’s place is clean, well kept and had all amenities needed for a snowy hiking and relaxing weekend. The indoor fireplace was amazing. There is someone else living on the property, out of sight and earshot. Very private, cozy property - the stream in the back was beautiful! Recommend highly!

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