
Holiday houses in Greenfield
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Top-rated holiday rentals in Greenfield
Guests agree: these stays are highly rated for location, cleanliness and more.

Soaring 2-level loft w/ views in heart of downtown
Walk to everything from this sunny, spacious 2-level, newly renovated 3rd-floor loft in downtown Shelburne Falls, right by the Bridge of Flowers. Cathedral ceiling, giant windows with views of mountains & river. Open upstairs queen bed space. Comfy pull-out queen bed downstairs. Washer/dryer. Well-equipped kitchen w/ dishwasher. Brand-new tiled shower. Fast Internet, two smart TVs, and a 15,000 BTU air conditioner that cools the big space in minutes. 15-minute drive to Berkshire East ski resort.

Charming Brookside Artisan Home
Relax, work & play in this peaceful country home built by a renowned furnituremaker and filled with handmade furniture and art. Explore the countryside, listen to the babbling brook & visit the many local family farms. There is a large firepit and plenty of outdoor activities at your doorstep, including biking, hiking, and x-country skiing. Come get away from it all while being only 10 minutes to Greenfield and the quaint village of Shelburne Falls. Easy 30 minute drive to the five college area.

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.

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.

Monadnock Sunrise Forest Hideaway
Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

Great Falls Private Suite
Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon. We are between downtown Turners Falls and Greenfield. If you're looking for a private and bright suite with beautiful natural light and a modern bohemian feel this is the space for you! Please note that there is a kitchenette but not a full kitchen. Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the CT River.

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!

Unique Private Studio w/Queen bed on second floor
Second floor studio with keyless entry and large eat in kitchen in quiet, rural, residential area. Outdoor yard space for guest use. 15 min. walk to country store, bakery, 2 pizza shops, gas station with Dunkins, library, and Post Office. Easy access to Rt 91 and Rt 2. Eight min drive to Greenfield, 15 to Brattleboro, 20 to Northampton. Close to Northfield Mt Hermon, Stoneleigh Burnham, Deerfield Academy and Thomas Aquinas College. Close to VT and NH and 30-90 minutes to many ski slopes.

Cozy loft apartment in adventurers paradise
Relax in our uniquely decorated loft apartment. This location is a privately secluded homestead, bordering the Maitland Memorial Forest. Just minutes from all of your favorite outdoor adventures! We are 10 mins from the Berkshire East Mountain Resort and the Deerfield river. We have bike storage and a great repair area. Amenities: Full kitchen and bath. we are happy to announce the completion of our new deck and private entrance for our guests that includes private yard and fire pit

Sweet Vermont Tiny Home Get Away
Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

Cozy one bedroom apartment
This is a beautiful one bedroom apartment located on the first floor that was recently remodeled. The stylish place is perfect for 2 people. It has a good size kitchen and a porch in the back. Located on a quiet and safe street yet close local restaurants and coffee shops. Easy hikes with great views like Poet Seat Tower and Highland Park. Also close to Deerfield Academy, Northfield Mount Hermon, The Bement School, Eaglebrook Schoool and Stonleigh-Burnham School.

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.
Popular amenities for Greenfield holiday rentals
Other great holiday rentals in Greenfield

Coziest Suite between Berkshire East and Mt. Snow

Spacious, Sunny* Woodland Retreat

Light-filled 3-br on park

Peaceful forest cottage getaway

Sunderland house - 5 College area

On the Water at North Bridge Cove, Patio and Sauna

4-guest apt, easy highway access, woodsy yard

Vermont Mirror House
When is the best time to visit Greenfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $160 NZD | $174 NZD | $175 NZD | $181 NZD | $196 NZD | $195 NZD | $182 NZD | $196 NZD | $198 NZD | $155 NZD | $139 NZD | $151 NZD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Greenfield?
Four-legged friends are welcome in Greenfield. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there family-friendly apartment rentals in Greenfield?
Greenfield has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in apartment rentals in Greenfield?
Experience the best of Greenfield with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Greenfield?
Yes! Work meets play with ease at over 10 vacation rentals in Greenfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do apartment rentals in Greenfield have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Greenfield. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Greenfield have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Greenfield. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Greenfield

Total holiday rentals
Explore 30 holiday rentals in Greenfield

Nightly prices starting at
Greenfield holiday rentals start at $87 NZD per night before taxes and fees

Verified guest reviews
Over 3,650 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Greenfield holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Greenfield rentals

4.9 Average rating
Greenfield stays are highly rated by guests—averaging 4.9 out of 5!
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- Six Flags New England
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- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Brimfield State Forest
- Mount Snow Ski Resort
- Norman Rockwell Museum
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- Mount Sugarloaf State Reservation
- Bromley Mountain Ski Resort
- Beartown State Forest
- Mount Tom State Reservation
- Crotched Mountain Ski and Ride
- Hildene, The Lincoln Family Home
- Berkshire Botanical Garden
- Hooper Golf Course
- Pineridge Cross Country Ski Area




