Cottage holiday rentals in Pioneer Valley

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Top-rated cottage rentals in Pioneer Valley

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

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Guest favourite

Cottage

4.96 out of 5 average rating, 142 reviews

Cedar Sunrise

Welcome to Cedar Lake. Come enjoy the lake and all it has to offer while staying in this cottage at the waters edge. This home may be small, but it offers a full kitchen with microwave, gas stove, Keurig and full size refrigerator. Open concept living, dining and kitchen. One bedroom with queen size bed, an open loft with a twin size bunk bed with trundle and a pullout couch in the living room. Full size bathroom with tub, washer & dryer on site. Enjoy grilling on the deck and soaking up the sun

Guest favourite

Cottage

4.94 out of 5 average rating, 176 reviews

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 • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • 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

Guest favourite

Cottage

4.99 out of 5 average rating, 182 reviews

Cider House Cottage

Antique guest cottage on a country 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.

Guest favourite

Cottage

4.89 out of 5 average rating, 180 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs .More than one dog will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

Guest favourite

Cottage

4.93 out of 5 average rating, 270 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Guest favourite

Cottage

4.99 out of 5 average rating, 152 reviews

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.

Superhost

Cottage

4.89 out of 5 average rating, 316 reviews

Romantic Private Vermont Cottage - Waterfront

Welcome to beautiful Southern VT! This is a private cottage located in Bennington, VT. The setting is picturesque, on a private lake with diverse wildlife, waterfall and covered bridge. Full kitchen, covered porch, loft bedroom and additional sofa bed. We provide every conceivable amenity for a comfortable stay. A unique retreat for a cozy and peaceful getaway. There is no other vacation property of this quality and character in southern Vermont. Enjoy mornings on your own private lake.

Guest favourite

Cottage

4.94 out of 5 average rating, 135 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Superhost

Cottage

4.84 out of 5 average rating, 289 reviews

Cozy Camp in Vermont

This cozy camp located in beautiful East Dover, is on a secluded road off the beaten path. Close to Mount Snow, Lake Whitingham, Lake Raponda, and only 25 minutes to Brattleboro the adventures are endless! Get out of the city and visit the serenity and beauty of Southern Vermont- especially in Fall during “leaf peeping”. This is a camp-style cottage with rustic charm. Newly replaced flooring and a fresh coat of paint in both bedrooms upstairs. Snow tires are a MUST- Nov.-April

Guest favourite

Cottage

4.94 out of 5 average rating, 121 reviews

Country Cottage in Goshen

Quaint country cottage, with beautiful hardwood floors, screened in porch, claw foot bathtub and lots of antiques set on a naturally landscaped 1 acre property. The original cottage was built in 1932, but was completely renovated in the last 5 years. 650 square feet with a bedroom, bathroom, lounge on the 2nd floor loft, and an open floor plan with living area, dining area and kitchen on the first floor. French doors lead from the dining area to a large screened in porch.

Guest favourite

Cottage

4.9 out of 5 average rating, 112 reviews

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Guest favourite

Cottage

4.94 out of 5 average rating, 270 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

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(will consider pets.)(90 second walk through wooded path to lake)