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Cottage vacation rentals in Pioneer Valley

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Top-rated cottage rentals in Pioneer Valley

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Cottage in Shutesbury

4.93 out of 5 average rating, 196 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.

Jan 16 – 23

€ 374 per night

Cottage in Petersham

4.99 out of 5 average rating, 150 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.

Jan 4 – 11

€ 153 per night

Cottage in Bernardston

4.88 out of 5 average rating, 286 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.

Mar 25 – Apr 1

€ 137 per night

Cottage in Florida

4.82 out of 5 average rating, 101 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.

Nov 12 – 19

€ 162 per night

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

-The Ice Pond Camp, East Dover, VT. Small well equipped country cottage, surrounded by nature & quaint beauty. Enjoy the lovely Southern Vermont seasons as you relax, disconnect, recharge & spend your days living a slower pace - surrounded by authentic rural beauty. Close to Wilmington and West Dover, (home of Mount Snow) and towns such as Putney and Brattleboro. Just minutes away are scenic villages, green farms, brooks,ponds and lakes, walking trails & country roads.

Jul 19 – 26

€ 136 per night

Cottage in Shaftsbury

4.99 out of 5 average rating, 598 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

Apr 13 – 20

€ 458 per night

Cottage in Orange

4.94 out of 5 average rating, 131 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.

Jan 19 – 26

€ 143 per night

Cottage in Becket

4.95 out of 5 average rating, 128 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.

Aug 17 – 24

€ 493 per night

Cottage in Becket

4.94 out of 5 average rating, 237 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)

May 5 – 12

€ 193 per night

Cottage in Orange

4.95 out of 5 average rating, 196 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.

Sep 13 – 20

€ 140 per night

Cottage in Ashfield

4.97 out of 5 average rating, 299 reviews

hope house

Sunny and open writing studio with over 150 years of literary history. Built in 1870, this lovely little house was where George Curtis edited Harper's magazine, wrote essays on transcendentalism , and argued for women's suffrage ( A recent guest informs me that George Curtis helped Thoreau build his cabin on Walden Pond ) The house has since sheltered painters, librarians, and poets.

Feb 16 – 23

€ 177 per night

Cottage in Granby

4.87 out of 5 average rating, 137 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

Jan 26 – Feb 2

€ 171 per night

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Pioneer Valley cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Great Barrington

4.93 out of 5 average rating, 235 reviews

Artist Cottage

Oct 20 – 27

€ 272 per night

Cottage in Litchfield

4.89 out of 5 average rating, 257 reviews

Litchfield - Hot Tub - Mohawk Mountain - Fireplace

Aug 19 – 26

€ 432 per night

Cottage in Southwick

4.97 out of 5 average rating, 64 reviews

4 Kayaks Lake View from Hot Tub Fire Pit Six Flags

Nov 16 – 23

€ 342 per night

Cottage in Burlington

5.0 out of 5 average rating, 41 reviews

Cozy Cottage w/Lakefront Views, Swim Spa & Firepit

Sep 24 – Oct 1

€ 386 per night

Cottage in Williamsburg

4.71 out of 5 average rating, 99 reviews

Northampton-area Hot tub Pet Friendly

Jun 11 – 18

€ 278 per night

Cottage in Eastford

4.89 out of 5 average rating, 75 reviews

Serenity Ashford Lake

Jul 14 – 21

€ 334 per night

Cottage in Rindge

4.79 out of 5 average rating, 53 reviews

Waterfront Cottage with a HOT TUB

Apr 6 – 13

€ 330 per night

Cottage in Woodstock

5.0 out of 5 average rating, 11 reviews

Lakefront Cottage Complete with Kayaks!

Mar 30 – Apr 6

€ 509 per night

Pet-friendly cottage rentals

Cottage in North Bennington

4.9 out of 5 average rating, 289 reviews

Romantic Private Vermont Cottage - Waterfront

Jul 18 – 25

€ 201 per night

Cottage in Windsor

4.89 out of 5 average rating, 164 reviews

In-law apartment in Farmington River Cottage

Jun 6 – 13

€ 109 per night

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

May 29 – Jun 5

€ 125 per night

Cottage in Lanesborough

4.85 out of 5 average rating, 250 reviews

Wildlife Lakeside Cottage

Feb 14 – 21

€ 305 per night

Cottage in Williamstown

4.9 out of 5 average rating, 165 reviews

Cute Cozy Comfy Cottage in the Berkshires

Jul 20 – 27

€ 203 per night

Cottage in Sharon

4.9 out of 5 average rating, 124 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

Jun 10 – 17

€ 220 per night

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 103 reviews

Cheerful 3-bedroom cottage with woodstove.

Nov 15 – 22

€ 292 per night

Cottage in Cornwall

4.94 out of 5 average rating, 116 reviews

Newly Built Cottage in Housatonic Valley

Nov 14 – 21

€ 256 per night

Private cottage rentals

Cottage in New Lebanon

4.94 out of 5 average rating, 175 reviews

The Writer's Cottage

Oct 31 – Nov 7

€ 119 per night

Cottage in Goshen

4.98 out of 5 average rating, 103 reviews

Country Cottage in Goshen

Jan 7 – 14

€ 157 per night

Cottage in Guilford

4.92 out of 5 average rating, 131 reviews

Peaceful Cozy Cottage in the Vermont Woods

May 29 – Jun 5

€ 132 per night

Cottage in Collinsville

4.96 out of 5 average rating, 112 reviews

The Carriage House

Dec 18 – 25

€ 192 per night

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

Stone School Cottage

Sep 5 – 12

€ 203 per night

Cottage in Great Barrington

4.98 out of 5 average rating, 126 reviews

Newly built cottage on working farm

Mar 11 – 18

€ 124 per night

Cottage in Guilford

4.97 out of 5 average rating, 105 reviews

Green River Cottage Retreat

Sep 23 – 30

€ 202 per night

Cottage in Chaplin

4.88 out of 5 average rating, 128 reviews

Clark Cottage in the historic village in Chaplin

Sep 5 – 12

€ 150 per night

Destinations to explore