
Waterfront holiday rentals in Pittsfield
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Top-rated waterfront rentals in Pittsfield
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Popular amenities for waterfront rentals in Pittsfield
Waterfront apartment rentals

Lovely 1 bedroom apt. with free parking in Rondout
Chris' place was even more beautiful than in the pictures. Location is perfect, within easy distance of the beautiful Kingston waterfront and nice restaurants. The area is quiet at night and felt very safe. Check-in was smooth and we had everything we needed. We'll definitely be staying there again on our next trip to Kingston.

**Happy Hour! Gorgeous & Modern Downtown Retreat**
Beautiful apartment in the center of Wilmington. We own land and have our camper set up in the next town over, but with the cold weather lately, the camper is still winterized. We wanted to come up and get some yard work done and stay locally, and this apartment was the clear winner! Walking distance to our favorite coffee shop, lots of restaurants, my favorite bookstore (!!) and walking trails. Loved the deck- even though it was April and iffy weather, we were able to have takeout dinner outside one night! So grateful that Jennifer allows pets, as we have two dogs and it’s often hard to find pet friendly Airbnb accommodations that are in a good location and as clean as this place! Jennifer was so kind, accommodating and responsive. She went out of her way to make sure we had a great trip- she’s definitely one of the best hosts we’ve had! Thank you for making this week wonderful! We will be back.

Sunny Peaceful Home
My daughter and I were seeking a basecamp to explore nearby colleges but also had one day where we needed to connect to our computers for work. We slept well, had peaceful morning walks in the neighborhood, took advantage of the sunshine on the lovely deck, and enjoyed making meals in the kitchen that had more than all the essentials.

Holland House: Modern Rustic Guest Apartment
Seth is definitely a “super host”! Instructions were very detailed and perfect! The suggestions for restaurants and things to do was extensive. The location was perfect for our visit to Valatie. I have never been to an Airbnb that was this clean - impeccable! The small back porch with a view of the river was awesome! I will definitely book this Airbnb again!

Globetrotter Retreat too - Minutes to the Mountain
Thanks for the host making this place like home. Furnitures are well organized. My partner and I love the sofa in the living room. There is a big sofa and single arm chair sofa. It’s good for staying with partner to kiss cuddle and more. We love the well organized kitchen. Very well-equipped. They even have some stock of food, coffee and tea bags just in case if you are hungry in mid night. We came here for skiing trip. It’s just 15 min to Mt Snow, 1.5h to Okemo. Stratton is also around this area. Great location for mountain staycation.

River View Apt in Shelburne Falls Historic Village
Thanks Crystal It was a great spot for the weekend and very comfortable!

DeMew Townhouse in Historic Kingston
Great place. Must try if you want quiet but right in the middle of it all

Majestic Farmhouse Private & Peaceful Guest Apt.
This was a quick trip to the area to break up the drive to a further destination. Joy's little 18thc apartment was perfect. Joy met and explained everything needed, and was very helpful with local suggestions for dining and activities.Was'nt here long enough to experience any of the hiking trails,.etc but truly seems like a place I'd like to return. if you're lucky, you will meet the inimitable Baloo!
Waterfront house rentals

Lakefront close to ski & shopping
A beautiful home and the views were breathtaking on the lake. Although, it was frozen. All the amenities we needed and more. Close to skiing and tubing. Owner Sara was very attentive to respond quickly. We just wanted a getaway place for a family weekend. The road was narrow and very icy. Would go back but not in the winter. Summer and the Fall I think would be best. Lots more things to do in the nicer weather months. Thank you Sara for your hospitality.

Private lakefront home, hot tub & resort amenities
This property was fantastic. The lake is beautiful, the kayaks and canoe offered by Vincent were in great condition and easy to use to explore the lake. And the house is well decorated, comfortable, and fits a large group easily. I would highly recommend a stay. Vincent is a great communicator and made the whole process easy — zero hassle whatsoever along the way.

Stylish Waterfront Escape on the Esopus Creek
We had a great stay at Rupert’s house. As other reviewers have stated, there is a train that passes by the house. Each day, it passed 2-3 times but it wasn’t terribly noisy. We never saw the tenant who also lives on the property. We didn’t realize that the tenant’s home was connected to the house we rented. It didn’t bother us but thought I’d share. Rupert was very responsive when we had questions. His home was a wonderful place for us to spend Thanksgiving. There was more than enough space for my family of 5. We especially loved the dining room with the long table and views of the Esopus Creek, which runs right behind the house. Given the weather, we didn’t spend time down there but it was certainly lovely to look at. We would definitely stay there again in the future.

Twin Island Lake House • Hot Tub
Anne Marie's place was exactly what we were looking for! It is extremely well stocked, with everything you might need, from kitchen appliances, extra blankets, many towels, etc. The surroundings were gorgeous and the area is very quiet and peaceful. Anne Marie was friendly and very responsive, answering questions quickly and flexibly. We can't wait to come back!

Majestic lake front house
This really was a perfect stay with an incredible view! We had an amazing stay at this Airbnb! The view was absolutely breathtaking, just as shown in the pictures. The bed was incredibly comfortable, and we felt right at home from the moment we arrived. The kitchen was spacious and well-equipped, making it easy to prepare meals. Everything was exactly as described, and we couldn’t have asked for a better experience. Highly recommend!

Upstate Riverfront Getaway with Hot tub
We always have a great stay at Matt’s! The amenities are amazing and the view of the Hudson is unbeatable.

Hudson Riverfront Mid-Century Modern Home
Clean, beautiful property. Excellent, accommodating hosts. Note dock is removed in winter and not available until May which was not reflected in original description but has been updated. We hope to return again.

Saratoga Lake Access | Private Dock | BEST Views!
Great location for a weekend getaway with beautiful lake views. Cottage felt like home and was within perfect driving distance of town.
Waterfront apartment rentals

Gorgeous Waterfront - Close to track & Saratoga
Nicholas was a great host and the place was awesome! Super clean and has everything you need. My dogs really liked looking out the big windows to the lake :)

LAKEFRONT: Walk to Marina, Restaurants, Near Track
This is our third time at Nick & Lynn’s! There is plenty of space to spread out, cook, dine, watch tv together and enjoy the incredible view and serenity of Saratoga Lake. Yes, will return!

Lakefront, dock, walk to marina and restaurants!
Nicholas was very responsive and accommodating. Beautiful place and well maintained.

Flowers & Falls Spot House
Superhost ! Was so accommodating to get us in last minute since our other Airbnb didn’t work out. He was so responsive and helpful with the snow storm as well ! We were so glad to have found this gem and have such a gracious host. The location is perfect and walkable to all the restaurants and markets. Also 15 mins away from Berkshire East ! This was a great find and we are thankful for it !
Quick stats about waterfront rentals in Pittsfield
Total rentals
20 properties
Nightly prices starting at
£75 before taxes and fees
Total number of reviews
870 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Stratton Mountain
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Six Flags New England
- Berkshire East Mountain Resort
- Taconic State Park
- Mount Snow Ski Resort
- Zoom Flume
- John Boyd Thacher State Park
- Mohawk Mountain Ski Area
- Mount Greylock Ski Club
- Mount Sugarloaf State Reservation
- Opus 40
- Norman Rockwell Museum
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Ekwanok Country Club
- Bright Nights at Forest Park