Cottage holiday rentals in Pioneer Valley

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Top-rated cottage rentals in Pioneer Valley

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Top Guest favourite

A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.

Cottage in Petersham

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

FamilyLocationCheckout

4.98 out of 5 average rating, 257 reviews

Top Guest favourite

Cottage in Brimfield

Cheerful cottage by Little Alum Lake & Sturbridge

Little Alum is a gorgeous spring-fed lake in the quintessential New England town of Brimfield, MA. Brimfield is known as home to the largest flea market in the country. Little Alum is regarded as one of the cleanest lakes in Massachusetts due to its pristine water quality. The charming cottage is a one level home within close proximity to highways & downtown Sturbridge and off route 20 just a few minutes to downtown Brimfield and Antique show/flea market. Partial water views, steps to the water.

LocationFamilyCondition

4.98 out of 5 average rating, 104 reviews

Top Guest favourite

A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.

Cottage in Becket

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.

LocationValueBeach

4.95 out of 5 average rating, 320 reviews

Top Guest favourite

An open living area features a dining table surrounded by wooden chairs. A comfortable sofa sits near a coffee table, with an air conditioning unit and a television mounted on the wall. Wooden beams adorn the ceiling, contributing to a cozy atmosphere.

Cottage in Bernardston

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Our quite and comfy home is conveniently located less than 2 miles from I-91, but a 1/4 mile down a country road giving you lots of privacy. The cottage is less than a mile from Crump 'N Fox Golf; 2 miles from Northfield Mount Hermon; 10 minutes from Greenfield & Stoneleigh Burnham; 15 min to Brattleboro, Deerfield Academy, Bement & Eaglebrook; 20 min to UMass, Amherst & Northampton; 30 minutes to Keene NH & Shelburne Falls and 45 min to the Basketball Hall of fame in Springfield & Mt Snow VT.

ValueFamilyComfort

4.88 out of 5 average rating, 369 reviews

Guest favourite

A serene lakefront home is nestled among tall trees, featuring a welcoming porch that overlooks the water. The exterior is painted in soft yellow, set against a backdrop of lush greenery. Nearby structures showcase a variety of architectural styles along the lakeshore.

Cottage in Shutesbury

Lake Wyola House Shutesbury Massachusetts

Bright, airy recently remodeled three Bedroom lakefront home on Lake Wyola. Most rooms have a Lake View. Beds and bedding are new, each bedroom has a ceiling fan. A super place to make awesome memories. Perfect for a family vacation or romantic getaway. (6 people, two cars max) Close to local colleges, Amherst, Northampton and many attractions. Comfortable and relaxing. Big Screen TVs in the living room and master bedroom. Cable and Wifi. Full kitchen, washer & dryer. Sorry no pets.

LocationFamilyIndoor spaces

4.92 out of 5 average rating, 249 reviews

Top Guest favourite

A hot tub with bubbling water is showcased under a covered patio, offering a view of the serene lake and surrounding trees. Soft lighting enhances the tranquil setting, while glimpses of the lake's shoreline and distant boats are visible in the background.

Cottage in Southwick

Lake Views from Deck Fire Pit & Hot Tub 4 Kayaks

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

FamilyLocationKitchen

4.98 out of 5 average rating, 167 reviews

Top Guest favourite

A cozy living area is presented with a wood stove, two windows allowing natural light, and a patterned area rug on the wooden floor. Chairs and a small table are arranged within the space, along with a decorative painting on the wall.

Cottage in Wendell

Cozy Scenic Cottage on Small Pond, Near Lake Wyola

Cozy, newly remodeled 2 bedroom cottage in a scenic location on a small pond. Serene views of woods and water make this a great place to relax and recharge. Hiking trails and lake swimming within walking distance. Very close to Lake Wyola. Amherst/UMass, Northampton, Quabbin, and Berkshire East all within 30-60 minutes. Perfect for small families (sleeps 3), couples, and outdoor enthusiasts. Includes full kitchen, washer/dryer, AC, RokuTV and fast WiFi internet. Sorry, no pets or smoking.

ValueLocationAccess

4.99 out of 5 average rating, 104 reviews

Top Guest favourite

A serene lake reflects the colors of twilight, with calm waters mirroring the darkening sky. A crescent moon is visible, while silhouettes of trees line the horizon. The scene captures the tranquil beauty of dusk over the peaceful landscape.

Cottage in Hinsdale

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.

LocationFamilyAccuracy

4.99 out of 5 average rating, 168 reviews

Guest favourite

A view from a framed window reveals a cozy living space featuring a vintage wood-burning stove. A green sectional sofa provides seating, complemented by a light wood coffee table. Natural light fills the room, highlighting the open layout connecting to the kitchen area.

Cottage in Becket

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,!

ValueLocationAccuracy

4.89 out of 5 average rating, 140 reviews

Guest favourite

A serene lake reflects a clear blue sky and lush green forests surrounding it. The water, calm and inviting, showcases the vibrant colors of autumn foliage along the banks, with tall grasses in the foreground adding to the natural landscape.

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. There is an incredible amount of wildlife, especially all types of birds. Sunny views abound. The house boasts a bright wood interior with a cozy feel. It has two and a half baths. There is a first floor queen bedroom with cathedral ceiling, and on the 2nd floor another queen room and a twin room-2 single beds.The adjacent lake teams with wildlife, seasonal weeds do grow. Contact us for conditions.

LocationFamilyParks

4.85 out of 5 average rating, 300 reviews

Top Guest favourite

An exterior view of the teahouse displays its rustic wooden structure nestled among lush greenery. A spacious wrap-around porch with wooden railings is visible, along with multiple windows allowing natural light. The surrounding foliage offers a natural ambiance.

Cottage in Falls Village

Retreat w 50 acre forest, waterfalls, tennis/bball

Perched above a brook in the woods. See the seasons fold and unfold in 50 acres of private forest, waterfalls, & pond. Fall asleep to sounds of the creek below. Wake to a canopy of beams, dappled sunshine, breakfast on a screened porch. Respite, creativity, and play (hike, sledding, 5 minutes from Mohawk Mtn Skiing). Hand built, inspired by Japanese teahouses, featuring tongue & groove construction, shoji screen doors, & tatami mats. Video: "Cornwall Hollow Teahouse" on YT or IG

LocationFamilyLong stay

4.99 out of 5 average rating, 133 reviews

Top Guest favourite

The cottage's exterior is composed of light blue siding, framed by lush greenery and mature trees. A paved pathway leads to the entrance, which features a modern black door. Sunlight filters through the leaves, creating dappled shadows on the grass.

Cottage in Amherst

Serene Modern Country Cottage near Amherst Center

A quiet, secluded setting while still walking distance to the restaurants, cafes, and shops of Amherst center, Amherst College, and 1.3 miles to UMass. Perfect for visiting academics, families, and anyone looking to experience the Happy Valley's unique charms. **Now featuring a HOT TUB on the private back patio!** We are pleased that the Cottage is powered, heated, and cooled by 100% renewable energy. We offer discounts for between 7-14 nights, please inquire.

LocationFamilyCheckout

4.96 out of 5 average rating, 121 reviews