Holiday rentals in Greenfield

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Top-rated holiday rentals in Greenfield

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Guest favourite

Flat in Shelburne Falls

4.98 out of 5 average rating, 485 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a newly 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!

18–25 Dec

$135 SGD per night

Guest favourite

Flat in Shelburne Falls

4.85 out of 5 average rating, 350 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.

22–29 May

$242 SGD per night

Guest favourite

Flat in Greenfield

4.98 out of 5 average rating, 154 reviews

Historic Greenfield Home: Cozy Private Guest Suite

Bright comfortable guest suite just blocks from lively downtown, yet quiet, private, and easy to park. The suite has one bedroom, one living room, and one newly renovated private bath; firm queen size mattress, crisp clean linens, Apple TV ready for your Netflix login, excellent high-speed wireless, private deck, and coffee bar stocked with coffee, tea, & snacks. You'll park in the rear of the house, and enjoy total privacy with your own entrance, key-code entry door; come and go as you please.

6–13 May

$203 SGD per night

Guest favourite

Cottage in Bernardston

4.88 out of 5 average rating, 285 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 Dec

$160 SGD per night

Guest favourite

Flat in Shelburne Falls

4.96 out of 5 average rating, 287 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.”

12–19 Mar

$140 SGD per night

Guest favourite

Flat in Greenfield

4.96 out of 5 average rating, 267 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Apartment: Entrance, bathroom & driveway are all private. Backyard with gas bbq. Kitchenette has microwave, toaster oven, Keurig coffee maker & sink. 2 TV’s one in living room & bedroom. Netflix, Amazon Prime , HBO & Local programs. High speed internet. Bedroom has Queen 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.

24–31 Jul

$143 SGD per night

Guest favourite

Guest suite in Greenfield

4.95 out of 5 average rating, 146 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. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to the Canadian border.

11–18 Mar

$95 SGD per night

Superhost

Guest suite in Montague

4.93 out of 5 average rating, 162 reviews

Great Falls Private Suite

Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the Connecticut River. Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon, 2 miles from downtown Turners Falls and 2.6 miles from downtown Greenfield. If you are looking for a private and bright suite with beautiful natural light and a modern bohemian feel this guest retreat is for you. I look forward to hosting you!

2–9 Jun

$136 SGD per night

Guest favourite

Loft in Shelburne Falls

4.95 out of 5 average rating, 262 reviews

The Railroad House

The Railroad House is a cute attached converted barn in the village center with parking, private entrance, 2 floors, fridge, microwave, coffee maker, toaster, WiFI, but no television. It is located within just a minute's walk from the famous Bridge of Flowers. Other local attractions include several dining choices from a drugstore soda shop on up to 5-star dining, as well as the country's 2nd oldest bowling alley. On weekends you can often find live music. Train goes by twice/day on average.

12–19 Sep

$125 SGD per night

Guest favourite

Guest suite in Sunderland

5.0 out of 5 average rating, 142 reviews

Bright private suite minutes to Five College area

Welcome to our bright, newly renovated suite in the historic Elihu Smith home, built in 1847. Centered on historic S. Main Street in Sunderland, we are minutes from UMass, Amherst, Hadley, Deerfield, and located on the local bus route connecting directly to UMass and Amherst. Ideal for stays of any length of time, for business or pleasure during any time of the year and walking distance to the Millstone market, as well the Bridgeside Café. Suite is professionally cleaned between each stay.

29 Aug – 5 Sep

$124 SGD per night

Guest favourite

Place to stay in Bernardston

4.95 out of 5 average rating, 332 reviews

Stylish Private Studio w/Queen bed and Coded Locks

Second floor studio with 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, brewery, 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.

12–19 Nov

$173 SGD per night

Guest favourite

Guest suite in Charlemont

4.9 out of 5 average rating, 181 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

21–28 Feb

$146 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Greenfield holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Greenfield's top sights

Big Y World Class Market13 locals recommend

Wagon Wheel Country Drive In11 locals recommend

Hope & Olive41 locals recommend

Green Fields Market18 locals recommend

Mesa Verde14 locals recommend

Foster's Supermarket12 locals recommend

Other great holiday rentals in Greenfield

Guest favourite

Guest house in Northampton

5.0 out of 5 average rating, 271 reviews

Mill River Cottage (pet friendly!)

20–27 Nov

$165 SGD per night

Guest favourite

Home in Williamsburg

4.99 out of 5 average rating, 157 reviews

Hilltown Studio

29 Dec – 5 Jan

$168 SGD per night

Guest favourite

Cottage in Petersham

4.99 out of 5 average rating, 148 reviews

Cider House Cottage

8–15 Nov

$189 SGD per night

Guest favourite

Cottage in Ashfield

4.97 out of 5 average rating, 299 reviews

hope house

4–11 Nov

$227 SGD per night

Guest favourite

Guest suite in Brattleboro

4.94 out of 5 average rating, 517 reviews

Charming studio in renovated 19th century church.

9–16 Dec

$127 SGD per night

Guest favourite

Flat in Winchester

4.93 out of 5 average rating, 160 reviews

Downtown Loft above Winery and Distillery

1–8 Nov

$110 SGD per night

Guest favourite

Guest house in Brattleboro

4.93 out of 5 average rating, 426 reviews

Mahalo Temple Retreat

3–10 Jul

$140 SGD per night

Guest favourite

Flat in Brattleboro

4.9 out of 5 average rating, 483 reviews

Cozy, Private & Great location for exploring VT !

4–11 Oct

$124 SGD per night

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Quick stats about holiday rentals in Greenfield

Total rentals	30 properties
Wifi availability	30 properties include access to wifi
Rentals with dedicated workspaces	20 properties have a dedicated workspace
Pet-friendly rentals	10 properties allow pets
Family-friendly rentals	10 properties are a good fit for families
Total number of reviews	2.8K reviews

Holiday rentals in Greenfield

Top-rated holiday rentals in Greenfield

Flat in Shelburne Falls

Flat in Shelburne Falls

Flat in Greenfield

Cottage in Bernardston

Flat in Shelburne Falls

Flat in Greenfield

Guest suite in Greenfield

Guest suite in Montague

Loft in Shelburne Falls

Guest suite in Sunderland

Place to stay in Bernardston

Guest suite in Charlemont

Holiday rentals for every style

Flats

Hotels

Unique stays

Popular amenities for Greenfield holiday rentals

Stay near Greenfield's top sights

Other great holiday rentals in Greenfield

Guest house in Northampton

Home in Williamsburg

Cottage in Petersham

Cottage in Ashfield

Guest suite in Brattleboro

Flat in Winchester

Guest house in Brattleboro

Flat in Brattleboro

Quick stats about holiday rentals in Greenfield

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore