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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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Cottage in Shutesbury

4.93 out of 5 average rating, 197 reviews

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 bed room 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 livingroom and master bedroom. Cable and Wifi. Full kitchen, washer & dryer. Sorry no pets.

6–13 Sep

€ 324 per night

Guest favourite

Cottage in Petersham

4.99 out of 5 average rating, 152 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.

19–26 Dec

€ 159 per night

Guest favourite

Cottage in Bernardston

4.88 out of 5 average rating, 287 reviews

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.

13–20 Mar

€ 134 per night

Guest favourite

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

14–21 Oct

€ 201 per night

Guest favourite

Cottage in Windsor

4.89 out of 5 average rating, 164 reviews

In-law apartment in Farmington River Cottage

If you are craving a getaway with a special someone, this space is meticulously clean and an opportunity to practice social distancing while relaxing and enjoying the Farmington River. Only 15 minutes from Bradley airport, 5 minutes from the train and I91. Nature, dining, all within a comfortable drive. You get it all here! Private space with its own entrance, one bedroom and newly updated bathroom, a cozy living room with fireplace in a Garden Level Unit. Off street parking available.

3–10 Jun

€ 111 per night

Cottage in Florida

4.82 out of 5 average rating, 102 reviews

Peaceful Mountain Cabin by Ski, Kayak, Museums +!

ENJOY A MOUNTAIN ADVENTURE You will fall in love with this magic cottage nestled within 2 acres of old growth forest. Breathe in the fresh air enjoying the mountain vistas and sipping some hot cocoa. Warm up by the pellet stove or gaze at the stars seating by the fire pit. Berkshire East Ski is a few min away as well as the famous hairpin turn and many national forests. MASS MoCA only 15 min away, and Mt. Greylock is nearby as well as many outdoor adventures, restaurants & pubs.

7–14 Apr

€ 164 per night

Guest favourite

Cottage in Goshen

4.98 out of 5 average rating, 103 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.

5–12 Nov

€ 157 per night

Guest favourite

Cottage in Orange

4.94 out of 5 average rating, 132 reviews

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.

25 Nov – 2 Dec

€ 142 per night

Guest favourite

Cottage in Becket

4.95 out of 5 average rating, 132 reviews

Cozy lakeside cottage

Two-bedroom cottage on the lake with a dock nestled in the woodsy Sherwood Forest Community. Relax with the whole family at our quiet and peaceful oasis. You can swim, fish, kayak, and canoe in the water right from our private beach. Great place for a lakeside campfire at night. Our dock is perfectly situated for practicing yoga, meditation or quiet contemplation. Please note that accessing the house as well as getting down to the dock requires climbing stairs.

5–12 Dec

€ 232 per night

Guest favourite

Cottage in Becket

4.94 out of 5 average rating, 238 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)

30 May – 6 Jun

€ 194 per night

Guest favourite

Cottage in Orange

4.95 out of 5 average rating, 199 reviews

The Fishing Cottage: A Sweetwater Stay

Located on the shore of Tully Pond, The Fishing Cottage is a newly 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.

19–26 Jan

€ 154 per night

Guest favourite

Cottage in Guilford

4.92 out of 5 average rating, 132 reviews

Peaceful Cozy Cottage in the Vermont Woods

Charming one bedroom cottage nestled in the Green Mountains of Southern Vermont. With all the comforts of a country retreat, the cottage is perfect for couples and can accommodate up to three adults. Just over three hours by car from New York City, two hours from the Boston area. The cottage and natural surroundings offer a chance to relax and unwind in a private, peaceful setting.

27 May – 3 Jun

€ 125 per night

Holiday rentals for every style

Get the amount of space that is right for you

Flats

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for cottage rentals in Pioneer Valley

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Lanesborough

5.0 out of 5 average rating, 11 reviews

Norte Maison 2 beds 2 Baths Minutes to Jiminy Peak

10–17 May

€ 342 per night

Cottage in Rindge

4.79 out of 5 average rating, 53 reviews

Waterfront Cottage with a HOT TUB

10–17 Apr

€ 318 per night

Guest favourite

Cottage in Eastford

4.89 out of 5 average rating, 75 reviews

Serenity Ashford Lake

20–27 Jun

€ 302 per night

Cottage in Williamsburg

4.71 out of 5 average rating, 99 reviews

Northampton-area Hot tub Pet Friendly

1–8 Jul

€ 291 per night

Guest favourite

Cottage in Southwick

4.97 out of 5 average rating, 65 reviews

4 Kayaks Lake View from Hot Tub Fire Pit Six Flags

10–17 Dec

€ 343 per night

Cottage in Monterey

4.88 out of 5 average rating, 8 reviews

mountain refuge

16–23 Sep

€ 167 per night

Cottage in Coventry

4.82 out of 5 average rating, 17 reviews

Lakefront Connecticut Retreat Near UConn

29 Jun – 6 Jul

€ 507 per night

Guest favourite

Cottage in Otis

4.96 out of 5 average rating, 28 reviews

Berkshire lakefront cabin with modern luxuries

12–19 Jun

€ 509 per night

Pet-friendly cottage rentals

Cottage in Lanesborough

4.85 out of 5 average rating, 251 reviews

Wildlife Lakeside Cottage

25 Apr – 2 May

€ 304 per night

Guest favourite

Cottage in Monroe

4.89 out of 5 average rating, 84 reviews

Pumpkin Pine Cottage: your next adventure awaits!

2–9 Mar

€ 151 per night

Guest favourite

Cottage in Warwick

5.0 out of 5 average rating, 19 reviews

By Still Waters Cottage

22–29 Apr

€ 304 per night

Guest favourite

Cottage in Winchester

4.93 out of 5 average rating, 27 reviews

Storybook Lake Front Villa with Private Beach!

30 Aug – 6 Sep

€ 342 per night

Guest favourite

Cottage in Guilford

4.97 out of 5 average rating, 67 reviews

The Blacksmith Shop

25 Jun – 2 Jul

€ 272 per night

Guest favourite

Cottage in Brimfield

5.0 out of 5 average rating, 31 reviews

Cheerful 2 bedroom cottage with lake access.

22–29 Jul

€ 207 per night

Cottage in Becket

4.76 out of 5 average rating, 139 reviews

Private Lake Cottage on 3 acres w/350 sq. ft. deck

28 Sep – 5 Oct

€ 373 per night

Cottage in Pittsfield

4.9 out of 5 average rating, 69 reviews

Cottage Getaway - access all the Berkshires offer!

5–12 Sep

€ 192 per night

Private cottage rentals

Cottage in Chaplin

4.88 out of 5 average rating, 129 reviews

Clark Cottage in the historic village in Chaplin

19–26 Mar

€ 154 per night

Guest favourite

Cottage in Hinsdale

4.99 out of 5 average rating, 141 reviews

Cozy Cottage in the Berkshires

30 Dec – 6 Jan

€ 264 per night

Guest favourite

Cottage in Guilford

4.97 out of 5 average rating, 105 reviews

Green River Cottage Retreat

24–31 Oct

€ 225 per night

Guest favourite

Cottage in Sturbridge

4.96 out of 5 average rating, 123 reviews

Cedar Sunrise

6–13 Oct

€ 260 per night

Cottage in Enfield

4.87 out of 5 average rating, 145 reviews

Hilda’s Riverside Retreat

18–25 Feb

€ 220 per night

Guest favourite

Cottage in New Marlborough

4.96 out of 5 average rating, 104 reviews

Converted Berkshire schoolhouse on a quiet river

15–22 Dec

€ 259 per night

Guest favourite

Cottage in Deerfield

4.97 out of 5 average rating, 90 reviews

Dreamy Guesthouse: sauna and private deck

3–10 Jan

€ 172 per night

Guest favourite

Cottage in Wendell

4.98 out of 5 average rating, 60 reviews

Cozy Scenic Cottage on Small Pond, Near Lake Wyola

7–14 Sep

€ 152 per night

Destinations to explore