Holiday houses in Conway

Apartment in Shelburne Falls

4.87 out of 5 average rating, 438 reviews

Big, sunny 1893 flat steps from Bridge of Flowers

Urban 3-room (2 bdrm) apartment on 3rd floor of funky older apt building on the main street of Shelburne Falls. Apartment faces the street, with views of the hills beyond. New kitchen appliances, and newly remodeled bath with custom shower, tile floor, and washer/dryer. Interesting art throughout the apartment, including some original pieces. Steps to the Glacial Potholes, Bridge of Flowers; and all the galleries, shops, restaurants, and cafes that this charming New England village has to offer.

5 out of 5 average rating, 117 reviews

Sunny Chalet Nestled in the Woods of Ashfield

Need some time to recharge surrounded by nature? Whether a group of friends, family or a wedding party - this property will suit all your needs. Access to hiking right out the door and loads of recreational activities such as skiing, swimming, biking. Our high speed WiFi and TV support streaming. Curl up on the couch and bask in the sunlight through the windows. Read a book by the fire. Gaze up at the stars and moon from the deck. Share a meal. A perfect spot for a retreat or family gathering.

Guesthouse in Shelburne Falls

5 out of 5 average rating, 274 reviews

Shelburne Guest House -The Ranch

The nice thing about my home in Shelburne is the location & the peace & quiet. 10 minute drive to Greenfield Rotary I-91, easy drive to Amherst, Smith, UMass, NMH, Deerfield Academy & Stoneleigh Burnham School. Berkshire East nearby for outdoor sports. 5 minute drive to the Village of Shelburne Falls, hiking trails, bike paths, High Ledges, & the Bridge of Flowers. Updated 1964 Sears Roebuck catalog home. Bright & sunny! Large farmhouse kitchen, 3 cozy bedrooms. Large yard! Your Vacation Home!

Guest suite in Greenfield

4.95 out of 5 average rating, 194 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

Apartment in Shelburne Falls

4.96 out of 5 average rating, 343 reviews

Annies’ Place by The Bridge of Flowers ~

As a guest at Annie’s Place, enjoy access to a tastefully, renovated 3 room apartment, including a fully equipped kitchen, living room, sofa with 2 recliners, a spacious bedroom, walk-in closet, full bath, TV & Internet. There is a seasonal front porch and mudroom for convenience. Meticulously maintained and located in the downtown village area. Simply park and walk to specialty shops, restaurants & the Bridge of Flowers. Shelburne Falls, designated as one of the 15 “Great Places in America.”

4.98 out of 5 average rating, 213 reviews

Cabin in Cummington

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Apartment in Shelburne Falls

4.97 out of 5 average rating, 559 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

4.97 out of 5 average rating, 154 reviews

Cottage in Deerfield

Dreamy Guesthouse: sauna and private deck

You will feel like you're deep in the country while being close to everything on this 11-acre homestead, surrounded by woods. Featuring an infrared sauna, breezy porch, and firepit, this private guesthouse (next to our residence) is a 15-min walk to Deerfield Academy, Bement, Eaglebrook, and Historic Deerfield; a short drive to all five colleges; and less than three miles from award-winning Treehouse Brewery. Halfway between Brattleboro and Northampton, this is the perfect valley spot.

4.97 out of 5 average rating, 271 reviews

Apartment in Plainfield

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

4.95 out of 5 average rating, 165 reviews

Apartment in Conway

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

4.96 out of 5 average rating, 409 reviews

Apartment in Greenfield

Mohawk Trail View/ private apt. no cleaning Fee

Small, cozy private Apt is located in West Greenfield in a quiet, safe neighborhood. Guests have own private driveway and entrance. There are 2 TV’s, one in living room & bedroom. High speed internet. Queen size bed & desk. Apt. Is 2 min's to Rt. 2, Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes

Superhost

Cabin in Plainfield

4.92 out of 5 average rating, 170 reviews

Peaceful Cabin in the Woods

Escape the noise and come relax in the middle of the beautiful Berkshire Hills. This classic log cabin has been recently renovated so that you can unwind and connect to the picturesque landscape that envelopes this property. You can drive 30 minutes west to North Adams and visit Mass Moca or 30 minutes east to Northampton, Amherst & Hadley. (Please note, 1/2 of the bedrooms is an open loft).

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Other great holiday rentals in Conway

5 out of 5 average rating, 16 reviews

J&J’s Retreat

SeanRating, 5 stars6 months ago

What a retreat! This was a lovely stay in a beautiful home which was well decorated and every little detail was thoughtful. Our family enjoyed our stay - thank you!

4.9 out of 5 average rating, 49 reviews

Luxury log style home with views to Mt. Monadnock!

SamRating, 5 stars2 months ago

We had a wonderful stay at Debra's log cabin. Beautiful location, glorious and cozy home, and fun amenities. We played foos-ball and spent many lovely, peaceful hours in the cabin. Be careful in the winter/early spring as the walkways and driveway can get icy, but it's worth it to make it up them both.

4.96 out of 5 average rating, 71 reviews

Cabin in Guilford

Guilford Grove Cottage

ElizabethRating, 5 stars5 days ago

We truly loved staying in this beautiful, cozy cabin. It was just the right size for the two of us, and very comfortable. The view of trees and wildflowers was lovely and refreshing. It was also fun to have a couple of cats walk across the porch each day! Joel was very proactive and friendly, which we greatly appreciated.

4.98 out of 5 average rating, 57 reviews

An 18th century farmhouse

NateRating, 5 stars6 days ago

What a beautiful, idyllic getaway Susan offers for her guests. A kind welcoming soul who provides a stay that brings you back in history – we had the most lovely time!

4.83 out of 5 average rating, 30 reviews

Cabin in Montague

Two Geese Cottage, Private Home For Getaways!

VenusRating, 5 stars3 weeks ago

My family and I had a wonderful stay at this cozy cabin cottage! Tucked away in a peaceful and remote area! The scenery was stunning, surrounded by nature, with complete peace :) The cabin itself was clean, well-equipped, and full of rustic charm. Everything we needed for a comfortable stay was thoughtfully provided. What truly made the experience exceptional were the hosts. They were incredibly responsive, going above and beyond to make sure we felt at home. You can tell they genuinely care about their guests' comfort and experience. If you're looking for a quiet retreat in a beautiful, secluded spot with amazing hosts, this is it. Highly recommend!

Apartment in Williamsburg

4.95 out of 5 average rating, 94 reviews

The cozy clubhouse

AronRating, 5 stars6 days ago

My wife and I had a wonderful stay at Karen’s guest house apartment! We couldn’t have asked for a more perfect location while in town for a wedding at Valley View farm, 2 min away. The property is also a very short distance from Northampton. Karen was proactive and reached out well in advance with clear instructions for parking and check-in. We mistakenly did not formally include our small dog in the reservation details, but she was extremely understanding and prepared with special blankets to cover the couch for us. The air conditioning kept us cool, the kitchen was extremely clean and well stocked, and the bathroom was great (lovely tiled shower). Plenty of towels. The yard was also lovely and perfect for walking our dog. Check out instructions were very simple and clear. Much quicker and expected less than other hosts. Next time we’re in Western mass, we will definitely stay with Karen again! 😊

4.91 out of 5 average rating, 23 reviews

Apartment in Greenfield

4-guest apt, easy highway access, woodsy yard

PaulRating, 5 stars3 days ago

This our first stay with Michael but we will look to book again. The space is clean, quiet and well supplied. The location is just minutes to downtown restaurants and shopping. The beds are comfortable with plenty of pillows and covers. We had a nice chat with Michael before we left. Be sure to pay close attention to his clear instructions to find the place or it could be difficult if you use your GPS.