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Waterfront vacation rentals in Pittsfield

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Top-rated waterfront rentals in Pittsfield

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Rental unit in Saugerties

5 out of 5 average rating, 3 reviews

Esopus Creekfront | Family | Game Rm | Kayaks

Welcome to Upstate Waterfronts! Whether you are traveling for the Holidays, visiting family, or looking for a restorative Upstate getaway - this Creekside gem has you covered. - 2 bedrooms/1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 52'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Home in Athens

4.94 out of 5 average rating, 114 reviews

Private lakefront home, hot tub & resort amenities

Stylish, and private Catskills lake-front house, w/ amazing lake views, a private hot tub, fire pit, beach and dock; community swimming pools, tennis, pickle ball, basketball courts, baseball fields, playgrounds, dog beach & parks, golf driving range. This home has all you need to entertain, and work from. Located 2hrs from NYC, 15-30 minutes from Catskill, Hudson, Woodstock, Hunter and Windham ski resorts, the best restaurants, hiking trails, art galleries, antique shops, and cultural centers.

Camper/RV in Saugerties

4.89 out of 5 average rating, 56 reviews

WATERFRONT on the Hudson oasis🎒🛶🎣🔥Bring your boat!

Waterfront vacation with access to the Hudson. Bring your boat, dock and launch. Guests enjoy access to kayaks, fishing poles, paddle boat and boat slip! Our Hudson River waterfront property has a large Recreational Vehicle with a private bedroom , seperate bathroom, roomy living room with sofa bed and great modern kitchen. Breathtaking views and large gazebo to enjoy outdoor dining. Great grill to bbq!!! Saugerties LightHouse Trail (0.2 Miles) EXTRA FEE FOR DOCKING BOAT $50 PER BOAT at

Cottage in Valatie

4.99 out of 5 average rating, 141 reviews

Kinderhook Lake Retreat-kayaks/SUP/central air

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying lake wildlife -Grab a kayak or paddleboard and explore the bays, coves and creeks -Catch the sunset, then end the day sharing stories around the starlit firepit An ideal base for exploring restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

Home in Pittsfield

4.97 out of 5 average rating, 106 reviews

Berkshire Pontoosuc Lake- Modern and Updated

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Cottage in Hudson

4.84 out of 5 average rating, 128 reviews

Peaceful waterfront getaway near Hudson, NY

Love nature? Enjoy your own entire home on the Stockport Creek with private kayak/boat launch to the Hudson River. Hiking and bike trails nearby. You are immersed in Columbia County’s rural beauty between the Berkshires and the Catskills with Hudson’s hopping food and art scene minutes away. OMI sculpture park, Olana, Chatham, farm markets, and Warren Street are a short drive. Ski Hunter or Catamount inside an hour. Cozy wood burning stove as well as outdoor fire pit. Minimum 3 day stay.

Home in Athens

4.93 out of 5 average rating, 114 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Cottage in Red Hook

4.9 out of 5 average rating, 201 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you. BE SURE TO SEE OUR OTHER 2 BEDROOM COTTAGE ON THE LAKE - LILY PAD - IF YOUR DATES ARE NOT AVAILABLE.

Home in Otis

4.9 out of 5 average rating, 51 reviews

Berkshire Lakefront Lighthouse Getaway

Escape to your own slice of paradise in our 450 Sq. Ft breathtaking Lighthouse rental on East Otis reservoir! This stunning property boasts a multi-level 800 square foot deck with jaw-dropping views of the shimmering Lake below making it the perfect place to unwind and soak up the natural beauty of Massachusetts. For water enthusiasts, the lighthouse rental also includes a 500 ft shared dock, providing easy access to the lake for swimming, fishing, kayaking and more.

Rental unit in Saugerties

4.86 out of 5 average rating, 147 reviews

Saugerties Marina Peaceful Setting On the Water

Comfort in the Catskills! Enjoy an affordable picturesque location! Newly renovated kitchen with all the comforts of home. We are minutes from HITS, Woodstock, Rhinebeck and a short distance to ski and hiking areas. Pets welcome, arrange prior to booking for our policies regarding pets. This home is the perfect peaceful getaway for boaters and water lovers. This charming 2 bedroom w/ full bath apartment is located on a dead end road and has off street parking.

Home in Saugerties

4.93 out of 5 average rating, 135 reviews

Upstate Waterfront Saugerties Retreat-Near HITS

Serene riverfront home, just outside the Village of Saugerties with strong Wifi for easy work-from-home. You can swim, canoe, fish on the banks of the Esopus direct from your own home. Bright and stylish space with clean aesthetic, direct water access with lovely views across the Esopus to a protected preserve - ideal for dinners on the deck in Summer or Fall. Or cozy up by the fireplace in Winter after skiing at Hunter, and binge on movies on the large TV.

Home in Otis

4.97 out of 5 average rating, 104 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

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Popular amenities for Pittsfield waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Rental unit in Wilmington

4.98 out of 5 average rating, 464 reviews

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

Rental unit in Hudson

4.94 out of 5 average rating, 103 reviews

The Big Blue House - 1st Floor Flat

Rental unit in Charlemont

4.99 out of 5 average rating, 144 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Rental unit in Valatie

4.95 out of 5 average rating, 183 reviews

Holland House: Modern Rustic Guest Apartment

Rental unit in Shelburne Falls

4.98 out of 5 average rating, 104 reviews

River View Apt in Shelburne Falls Historic Village

Rental unit in Newfane

4.97 out of 5 average rating, 433 reviews

Rock River Retreat: VT Oasis Pet Friendly

Rental unit in West Granby

4.9 out of 5 average rating, 130 reviews

Majestic Farmhouse Private & Peaceful Guest Apt.

Rental unit in Craryville

4.92 out of 5 average rating, 113 reviews

Captain's Quarters at Mickey's Marina

Waterfront house rentals

Home in Saugerties

4.82 out of 5 average rating, 90 reviews

Stunning & Unique Hudson River Views

Home in Averill Park

4.98 out of 5 average rating, 170 reviews

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

Home in Southwick

4.77 out of 5 average rating, 26 reviews

My Lake House w/dock and kayaks

Home in Craryville

4.91 out of 5 average rating, 46 reviews

Cozy Lakefront House close to Ski Mountains

Home in Athens

5 out of 5 average rating, 20 reviews

Modern 4 season lakefront rental

Home in Pine Plains

4.98 out of 5 average rating, 120 reviews

Twin Island Lake House • Hot Tub

Home in Valatie

4.96 out of 5 average rating, 24 reviews

Majestic lake front house

Home in Becket

4.93 out of 5 average rating, 29 reviews

Lakefront Cottage on Private Beach

Quick stats about waterfront rentals in Pittsfield

Total rentals
20 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
910 reviews
Family-friendly rentals
20 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

Destinations to explore