Waterfront vacation rentals in Pittsfield

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Pittsfield waterfront rentals

Waterfront apartment rentals

Superhost
A cozy living area is featured with a dark leather sofa and a light-colored armchair. A glass coffee table sits atop a patterned area rug. Wall sconces provide soft lighting, while a television and decorative fireplace are visible, enhancing the space's comfort.
Apartment in Pittsfield
5 out of 5 average rating, 4 reviews

Lavishly Appointed 2BR Apt. Home

RachelRating, 5 stars6 months ago
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!
Guest favorite
A well-lit kitchen and dining area features a wooden dining table surrounded by six chairs. Light hardwood flooring complements the gray cabinetry. A potted plant sits on the table, and modern appliances are visible in the background, including a refrigerator and stove.
Apartment in Wilmington
4.98 out of 5 average rating, 481 reviews

**Happy Hour! Gorgeous & Modern Downtown Retreat**

LisaRating, 5 stars1 week ago
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.
Top guest favorite
A cozy lounge area is presented with a grey sofa and two white armchairs, set against a green wall. Natural light fills the space through large windows, highlighting the light wood flooring. A ceiling fan adds comfort, while a small lamp provides additional illumination.
Apartment in Charlemont
4.99 out of 5 average rating, 157 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

MichelleRating, 5 stars1 month ago
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!
Top guest favorite
A spacious light-filled living area features a comfortable sectional sofa adorned with decorative pillows. Two framed floral prints hang on the wall above. A wooden table with chairs is visible nearby, along with a shelf containing various toys and books, enhancing a family-friendly space.
Apartment in Northampton
4.92 out of 5 average rating, 617 reviews

Sunny Peaceful Home

NidisRating, 5 stars3 weeks ago
Everything was amazing. The area, the place, the kitchen, the backyard we love it. 1000% recommended!!
Guest favorite
A modern living area is furnished with a gray sectional sofa and an accent chair. A wooden coffee table sits between them on a light rug. Natural light filters through large windows, illuminating a mirror mounted on the wall. Decorative pillows add a pop of color.
Apartment in Valatie
4.95 out of 5 average rating, 189 reviews

Holland House: Modern Rustic Guest Apartment

JulieRating, 5 stars1 month ago
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!
Top guest favorite
A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.
Apartment in Wilmington
4.91 out of 5 average rating, 134 reviews

Globetrotter Retreat too - Minutes to the Mountain

XianlongRating, 5 stars3 weeks ago
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.
Guest favorite
A cozy living room features a brown leather sofa adorned with patterned cushions. A coffee table with decorative items sits in front of the sofa, while a large window allows natural light to illuminate the space. A potted plant and artwork decorate the room, enhancing its charm.
Apartment in Shelburne Falls
4.97 out of 5 average rating, 117 reviews

River View Apt in Shelburne Falls Historic Village

AllieRating, 5 stars1 week ago
Thanks Crystal It was a great spot for the weekend and very comfortable!
Top guest favorite
Apartment in Newfane
4.97 out of 5 average rating, 448 reviews

Rock River Retreat: VT Oasis Pet Friendly

AshleyRating, 5 stars6 days ago
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

Guest favorite
A dining area features a wooden table surrounded by six chairs, with two additional seats visible. Large glass doors provide a view of Glass Lake, while warm wood paneling and beams create an inviting atmosphere. Natural light floods the space, enhancing its connection to the outdoors.
Home in Averill Park
4.98 out of 5 average rating, 174 reviews

Lake House in Averill Park, NY (age 30+ excl kids)

KathleenRating, 5 stars3 weeks ago
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!
Superhost
An aerial view captures the serene landscape surrounding Congamond Lake, highlighting lush greenery and residential areas along the water's edge. Several boats are visible on the lake, and the peaceful ambiance of the community is evident in the well-maintained homes and natural surroundings.
Home in Southwick
4.78 out of 5 average rating, 27 reviews

My Lake House w/dock and kayaks

NancyRating, 5 stars3 months ago
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.
Guest favorite
A covered porch features comfortable seating arrangements with wicker sofas and a coffee table. The view overlooks a serene lake, framed by trees and a cloudy sky. The patio area offers potential for relaxation, with easy access to lovely outdoor scenery.
Home in Craryville
4.91 out of 5 average rating, 46 reviews

Cozy Lakefront House close to Ski Mountains

SamanthaRating, 5 stars6 months ago
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.
Guest favorite
Home in Athens
5 out of 5 average rating, 20 reviews

Modern 4 season lakefront rental

KatieRating, 5 stars6 months ago
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!
Guest favorite
A covered porch features comfortable seating with soft cushions, offering expansive views of the lake and surrounding trees during sunset. The warm light casts a golden hue, enhancing the serene outdoor space, while a small table sits in the center, inviting relaxation.
Home in Pine Plains
4.98 out of 5 average rating, 122 reviews

Twin Island Lake House • Hot Tub

CoryRating, 5 stars3 months ago
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!
Guest favorite
A bright living space features large floor-to-ceiling windows that allow natural light to fill the room. A cozy seating arrangement includes modern chairs and a round coffee table on a patterned rug, with a view of the trees and lake visible through the glass.
Home in Valatie
4.97 out of 5 average rating, 30 reviews

Majestic lake front house

MagdalenaRating, 5 stars2 months ago
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!
Superhost
The exterior view highlights a modern two-story home surrounded by lush landscaping. A spacious deck is visible on the upper level, complemented by outdoor seating below. A hot tub and dining area with a patio umbrella can be seen on the stone patio, creating inviting spaces for relaxation.
Home in Cementon
4.91 out of 5 average rating, 107 reviews

Upstate Riverfront Getaway with Hot tub

TaylerRating, 5 stars1 month ago
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 :)
Superhost
Home in Saratoga Springs
4.8 out of 5 average rating, 5 reviews

Saratoga Lake Access | Private Dock | BEST Views!

AlexRating, 5 stars6 months ago
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

Guest favorite
A spacious dining area features a large table, surrounded by dark wooden chairs. Large glass doors provide stunning views of the calm lake and open to a deck. Bright natural light illuminates the sleek black countertops and modern appliances in the adjacent kitchen.
Condo in Saratoga Springs
4.84 out of 5 average rating, 44 reviews

Gorgeous Waterfront - Close to track & Saratoga

RyanRating, 5 stars2 months ago
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 :)
Top guest favorite
A spacious deck with a table and chairs overlooks a calm, expansive lake. A wooden dock extends into the water, with several boats visible at the dock. The tranquil scene is set under a partially cloudy sky.
Condo in Saratoga Springs
4.82 out of 5 average rating, 68 reviews

LAKEFRONT: Walk to Marina, Restaurants, Near Track

GinaRating, 5 stars3 months ago
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!
Guest favorite
A living room area features a large sectional sofa and a vibrant area rug. Sliding glass doors provide a clear view of the patio and the lake beyond, allowing natural light to fill the space.
Condo in Saratoga Springs
4.97 out of 5 average rating, 32 reviews

Lakefront, dock, walk to marina and restaurants!

KathleenRating, 5 stars3 weeks ago
Nicholas was very responsive and accommodating. Beautiful place and well maintained.
Superhost
A spacious light blue deck is shown, furnished with a small table and two white chairs. The surrounding area features greenery and a distant view of rolling hills, providing a serene outdoor space for relaxation.
Condo in Shelburne Falls
4.91 out of 5 average rating, 46 reviews

Flowers & Falls Spot House

MelanieRating, 5 stars2 months ago
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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