Vacation rentals with beach access in Pioneer Valley

House Above the Hollow

A lovely peaceful spot set in the beautiful rolling hills of Conway Massachusetts, overlooking historic Pumpkin Hollow. In close proximity to Shelburne Falls, Deerfield, Greenfield, Amherst and Northampton along with the famed Tree House Brewery, just 10 min away. There are many sights, country roads, trails to explore, along with many varied restaurants to enjoy. "One of the most peaceful, scenic places I've ever stayed. You can really hear yourself think." Kathy Connolly Old Sabyrook CT.

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

Whole place,staycation,3 bedrooms, spacious area

ENTIRE LIVING SPACE: Private spacious 3 bedroom lower level. Near MacDuffie Prep School & 5 prestigious colleges. Couples, solo adventurers, business travelers, families (with kids), and big groups. 14 acre. Private-golf course, pickleball, polypropylene basketball court, badminton, fishing, frisbee golf and tennis courts close by. Nature surrounds you with quiet locations to relax. 1 acre beach pond to cool off. If you are the person who likes to stay busy or relax, this is the place for you.

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere

Welcome to Lake Ashmere! Our newly and completely renovated cottage features two bedrooms with comfy queen size beds, a loft with two full size beds, cathedral ceilings, a year-round six person hot tub and a large working kitchen stocked with everything you need. The living space is bright and airy. WiFi in the cottage is over 500 mbps, making it ideal for longer stays. The spectacular lake is just a three-minute walk from the cottage and has a kayak and inner tubes available to our guests.

Cozy Cottage in the Berkshires

Come and enjoy our "happy place" year round! Our cozy, neat as a pin cottage is located in the beautiful Berkshires with gorgeous Ashmere lake views, spectacular flower beds and beach/lake access. Summer, fall, winter or spring, the cottage welcomes you, complete with a gift basket and fresh flowers. Enjoy the view of the lake off the spacious deck or play games in the grassy yard complete with fire pit for roasting marshmallows. Waterfront is only a minute or two walking distance away.

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

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

Sunny Chalet Nestled in the Woods of Ashfield

Relax in a quiet sunny chalet located on land with established herbal gardens, offering privacy, space, and a comfortable base for families and small groups visiting Ashfield and the surrounding hills. This pet-friendly three-bedroom home is designed for guests who want a peaceful, rural stay with the reassurance of an attentive host nearby. Whether you’re visiting family, exploring the area, or enjoying time away from the city, the chalet offers room to unwind in a calm setting.

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

The Fishing Cottage: A Sweetwater Stay

Located on the shore of Tully Pond, The Fishing Cottage is a designed vacation home with breathtaking views of Tully Mountain. This 4-season Cottage has real salvaged barn wood walls; up-cycled maple floors and one-of-a kind scratch built furniture and lighting fixtures. The deconstructed architecture leaves exposed the electrical conduit and copper plumbing pipes, making the cottage feel alive and organic.