
Waterfront vacation rentals in Pittsfield
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Top-rated waterfront rentals in Pittsfield
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Waterfront apartment rentals

Lavishly Appointed 2BR Apt. Home
A charming place and cozy stay! Robert was responsive and friendly. Also, I highly recommend the shrimp and cheddar grits at District Bar & Kitchen which is only a few minutes away. So good!

**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.

Suite 23 - Spacious Sunny 2-BR with Mountain view
We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

Sunny Peaceful Home
Everything was amazing. The area, the place, the kitchen, the backyard we love it. 1000% recommended!!

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!

Rock River Retreat: VT Oasis Pet Friendly
Truly a magical place… the views are amazing. We actually frolicked in the river a bit even though it’s only April and there was small amount of snow on the ground… it was surprisingly refreshing for a feet dip… as far as the unit there was so much charm and care put into this place… we had a snack and beverage awaiting us and Carmella the cat had a snack and toy with a little pillow bed by the window and food dishes ready to use. These extra little touches are special ❤️ The inside is super cute and charming, I loved the bath tub…. I stayed 2 nights and took 3 baths 😂 after our 5 hr drive my daughter needed to use facilities but it took her a good 10 minutes because she loved every detail of the space. I hope to return in summer! Book this space if interested, I promise you will not be disappointed!
Waterfront house rentals

Lake House in Averill Park, NY (age 30+ excl kids)
First of all, a 1 o’clock check in started us off on a very happy note. Then, having room for each female to have her own bed made a for peaceful stay. The biggest thing was how much the space was warm, comforting, and full of character. The sliders provided a broad view of the lake. The kitchen with the open area to dining and front area provided an open concept feel to an older home while maintaining its true character. The tall cabinets contained every utensil/small appliance that we needed and more. We brought a bag of board games as we know what we like, but there was a great variety already there. While there was plenty of room, we felt “together” in that space. We can only imagine the beauty that arrives later in spring. Thank you for having us!

My Lake House w/dock and kayaks
Spent a wonderful week during Christmas here with my adult son whom I hadn’t seen in years. Launa went above and beyond with making the home cozy and comfortable and the Christmas decor was more than I could have imagined. Launa allowed an early check in although I had an emergency which did not allow me to check in early but she offered me the option. Launa also allowed us a late check out which was very much appreciated. The only thing I wished was that the beds were a little less firm as I found them to be too firm but that’s just my preference. Very tranquil place and many memories were made. I would love to stay again perhaps during warmer months to enjoy the lake and outdoors but all in all it’s a beautiful home.

Cozy Lakefront House close to Ski Mountains
Wonderful, attentive, and responsive hosts! Their home is in a beautiful location, with views of/ access to the lake. We would love to come back.

Modern 4 season lakefront rental
An amazing house for a family stay in the Catskills area. Antonia has designed a beautiful home, with so many unique retro nods and details. The basement is an awesome additional space for everyone to hang out in. The backyard set up is also great- with easy access to the hot tub and a few steps to the lake. 15 min drive to great restaurants and things to do-Loved our stay here!

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
Would absolutely stay here again! House was super clean and beautiful, had plenty of kitchen appliances to cook in the nice kitchen. We loved being a close drive to Saugerties and Hudson. & the hot tub was great of course :)

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 condo 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
ﺩ.ﺇ367 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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- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Opus 40
- John Boyd Thacher State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Bright Nights at Forest Park
- Berkshire Botanical Garden
- Butternut Ski Area and Tubing Center