
Waterfront holiday rentals in Pioneer Valley
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Pioneer Valley
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

Rustic Pond Cabin: Nature, Stars & Serenity
Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. Pure clean pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay and walk the trail around the pond, have campfires outside in firepit! Cleaned by me, no crazy rules. Surrounded by nature! Private Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires!

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Chalet Sonsie: A Sweetwater Stay
Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

The Red Cabin-Secluded Getaway with backyard Brook
Welcome to our secluded mid-century cabin nestled in the foothills of the Berkshires in Northwestern CT! When you stay here you'll find over three private acres of ferns, forests, wild flowers and a native trout brook a stone's throw from the backdoor with your private hot tub to relax in. Beyond the brook are hundreds of acres of state forest preserve. Enjoy great hiking, fishing, skiing, antiques and restaurants minutes away. Only 2 hours from NYC and 8 minutes to Historic Norfolk Center.

Hadley Hay House | No Cleaning fees!
Rest easy in this picturesque, very spacious tranquil home ready for you for a relaxing stay. Minutes from umass, 10min to either Amherst or Noho. Not only will you have access to the hot tub and walk in the hay fields behind the house but we are directly across from the Connecticut River. Perfect spot for swimming or kayaking. Enjoy a beautiful view of the mountains/hay and corn fields from multiple rooms in the house. This space is above an all female wood working shop, happy to give tour!

Peaceful Lake Views from Private Hot Tub
Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for a week long getaway with 2 work spaces. 25 minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

River front guest suite
Unique 2 bedroom guest house on the Connecticut River in South Hadley, Sleeps 4 adults and two children. Bunk bed top for children or pull out of 4 adults. 1 bathroom Kayaking Paddle bikes and boards Fire pit Tour boat next door at Brunelle’s Patio Boathouse restaurant Village commons 1 mile away McCrays farm 1 mile away Ledges golf course 2 miles away Malls etc. 15 min MGM casino 15 min Basketball hall of fame 15 min Airport 45 min Amtrak 10 min Mt sugarloaf 20min. Hiking trails l

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D
The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

AirbytheStream waterfront, private, clean and cozy
Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.

Sunrise on the Water's Edge - Riverside Bungalow
Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Hill-Ross Guest Suite
You'll have the Guest Suite at The Historic Hill-Ross Homestead with private entrance all to yourself. Guest Suite is the renovated carriage house ell off the main farmhouse which houses 2 bedrooms, 1 kitchen, 1 living room and 1 bathroom including your own private patio. One bedroom has a queen bed and second bedroom has a full bed and a single bunk bed. Hill Ross Homestead is a short, 5 minute walk into downtown Florence.

Hilltown Cabin Hideaway: A River Runs Through It!
Rediscover peace in the Hilltowns of Western Mass. Charming 3BR cabin in nature, with full kitchen, bath, laundry, TV and Wifi! Relax in a serene, wild and beautiful place. Cook a meal with friends. Take a riverside hike, or explore an Old Growth Forest nearby. Go fishing. Watch fireflies. Jump in a swimming hole. Lie in the meadow. Watch the clouds. Enjoy the Hot Tub for two. *Breath the free air again!*
Popular amenities for Pioneer Valley waterfront rentals
Waterfront apartment accommodation

1st Floor The Inn at Highland Lake

Suite 23 - Spacious Sunny 2-BR with Mountain view

Modern Cozy Studio

3 BR with Private Balcony & Deck

Riverside Retreat – Cozy 2-Story Getaway!

Enjoy every season the Berkshires have to offer.

Majestic Farmhouse Private & Peaceful Guest Apt.

Riverfront White Beauty Home 2BD
Waterfront house rentals

Farm House of Hadley

Lake front retreat - Stylish Berkshire home

Green River Cottage-A Peaceful Country Retreat

Scenic River View

Little Longbow Lakefront Chalet

Direct Lakefront Home on Otis Reservoir Giant Yard

Idyllic family retreat - spacious lake home,

Charming Riverfront Cottage
Other waterfront holiday rentals

My Lake House w/dock and kayaks

Lakefront Lovely Cottage

Lakefront Retreat 30 min to Mt Snow & Berkshire Ea

Hummingbird Haven

Lux on the River near Tanglewood w/220v EV charge

Forget-Me-Not by AvantStay | Bold Lakefront Escape

Gorgeous Vermont Lakefront with epic sunsets!

Serene Lakefront Retreat
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
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- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Pet-friendly rentals Pioneer Valley
- Rentals with a fire pit Pioneer Valley
- Bed and breakfasts Pioneer Valley
- Cabin rentals Pioneer Valley
- Rentals with a kayak Pioneer Valley
- Condo rentals Pioneer Valley
- Rentals with a patio Pioneer Valley
- Rentals with pools Pioneer Valley
- Rentals with breakfast Pioneer Valley
- Apartment rentals Pioneer Valley
- House rentals Pioneer Valley
- Rentals with a washing machine and dryer Pioneer Valley
- Guesthouse rentals Pioneer Valley
- Family-friendly rentals Pioneer Valley
- Rentals with lake access Pioneer Valley
- Rentals with a fireplace Pioneer Valley
- Rentals with beach access Pioneer Valley
- Rentals with an EV charger Pioneer Valley
- Smoking-friendly rentals Pioneer Valley
- Rentals with outdoor seating Pioneer Valley
- Cottage rentals Pioneer Valley
- Private suite rentals Pioneer Valley
- Rentals with a hot tub Pioneer Valley
- Waterfront rentals Massachusetts
- Waterfront rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Ski Sundown
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- University of Massachusetts Amherst
- Connecticut Science Center
- Smith College
- Hilltop Orchards Home of Furnace Brook Winery
- Clark University
- Balderdash Cellars
- Old Sturbridge Village
- Bash Bish Falls




