Greenfield Holiday Rentals, Massachusetts: Private House Rentals

A snow-covered town with a prominent church steeple, red brick buildings, and a clear blue sky.

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Go beyond your typical stay in Greenfield

Pet friendly

Pool

Apartment

Family friendly

Condo

Hot tub

Waterpark

Cottage

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Our top choices for Greenfield hotels

Pet-friendly

Breakfast included

Reserve now, pay later

Hotel

Budget

1. Hampton Inn & Suites Greenfield

Greenfield

Matthew

฿5,786

฿6,462 total

includes taxes & fees

30 Aug - 31 Aug

2. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

Katie

฿3,230

฿3,607 total

includes taxes & fees

7 Sept - 8 Sept

Superior Suite, 1 King Bed with Sofa bed | Living area

3. Deerfield Inn

Deerfield

Jonathan

฿8,061

฿10,437 total

includes taxes & fees

1 Sept - 2 Sept

4. The Inn At Crumpin Fox

Bernardston

Christopher

฿5,309

฿5,930 total

includes taxes & fees

30 Aug - 31 Aug

Deluxe Room, 1 Queen Bed, Valley View | In-room dining

Deluxe Room, 1 Queen Bed, Valley View | Television

5. Windmill Motel Restaurant

Bernardston

Dan

฿3,972

฿4,436 total

includes taxes & fees

29 Aug - 30 Aug

6. Hotel UMass

Amherst

Kathryn

฿3,598

฿4,065 total

includes taxes & fees

13 Sept - 14 Sept

7. Comfort Inn & Suites Hadley - Amherst

Hadley

Uday

฿4,823

฿5,388 total

includes taxes & fees

9 Sept - 10 Sept

8. Homewood Suites by Hilton Hadley Amherst

Hadley

Doreen

฿5,602

฿6,258 total

includes taxes & fees

7 Sept - 8 Sept

9. Hampton Inn Hadley-Amherst Area

Hadley

SHAWN

฿4,276

฿4,777 total

includes taxes & fees

27 Sept - 28 Sept

10. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Marnie

฿5,524

฿6,077 total

includes taxes & fees

13 Sept - 14 Sept

11. Centennial House

Northfield

Amy

฿5,867

฿6,201 total

includes taxes & fees

30 Aug - 31 Aug

12. Vikings Villages Resort

Guilford

Juli

฿4,900

฿5,714 total

includes taxes & fees

20 Sept - 21 Sept

13. Hotel Northampton

Northampton

steven

฿4,854

฿5,422 total

includes taxes & fees

21 Sept - 22 Sept

Suite, 1 King Bed with Sofa bed, Non Smoking

14. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Morgan

฿3,862

฿4,248 total

includes taxes & fees

6 Sept - 7 Sept

15. Courtyard by Marriott Hadley Amherst

Hadley

Carlos

฿5,266

฿5,882 total

includes taxes & fees

7 Sept - 8 Sept

16. Fairfield Inn & Suites Springfield Northampton/Amherst

Northampton

rob

฿4,973

฿5,555 total

includes taxes & fees

13 Sept - 14 Sept

17. River Valley Inn

West Hatfield

Michael

฿3,029

฿3,383 total

includes taxes & fees

7 Sept - 8 Sept

18. Black Walnut Inn

North Amherst

Kelly

฿5,728

฿6,398 total

includes taxes & fees

14 Sept - 15 Sept

19. Inn on Boltwood

Amherst

Starling

฿6,009

฿6,712 total

includes taxes & fees

7 Sept - 8 Sept

Suite, 1 King Bed with Sofa bed, Non Smoking (Exterior Corridor)

20. Quality Inn & Suites Northampton - Amherst

Northampton

Sara

฿4,321

฿4,827 total

includes taxes & fees

27 Sept - 28 Sept

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Stay near popular Greenfield attractions

A vintage car parked under a brick archway.

Old Greenfield Village

8.0/10 (18 reviews)

Step back in time at Old Greenfield Village, where authentic 19th-century buildings showcase New England life circa 1895. Explore the General Store, blacksmith shop, and ice cream parlour filled with original artefacts.

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A windmill with a red door and window, surrounded by trees and a clear sky.

Energy Park

8.6/10 (17 reviews)

Energy Park combines environmental education with local history, showcasing renewable energy exhibits and a restored 1944 caboose. Explore native gardens or enjoy summer concerts at this free community greenspace.

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Greenfield Beach

8.0/10 (8 reviews)

This natural river swimming area offers a sandy beach and clear waters surrounded by mature shade trees. Families can enjoy picnic areas, athletic courts, and a toddler play area in this serene local retreat.

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Poet's Seat Tower

9.4/10 (24 reviews)

This historic sandstone tower offers panoramic views of Greenfield and the Pioneer Valley from atop Rocky Mountain. Climb the internal staircases at sunset to capture the Connecticut River valley bathed in golden light.

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Eunice Williams Covered Bridge

This historic covered bridge marks where Eunice Williams was killed during the 1704 Deerfield Massacre. Enjoy the tranquil setting over the Green River while exploring one of Massachusetts' few remaining covered bridges.

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Sammy K's Golf

Enjoy a round of golf in Greenfield at Sammy K's Golf. Take some time to visit the shops in this family-friendly area.

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Leyden Wildlife Management Area

Explore diverse habitats from forests to fields in this peaceful conservation area. Hikers can spot wildlife while traversing trails that lead to spectacular hilltop vistas of the Massachusetts countryside.

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Museum of Our Industrial Heritage

This intimate museum showcases Franklin County's industrial legacy through artefacts from cutlery to textiles, revealing how local ingenuity shaped American manufacturing while connecting past to present.

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Learn more about Greenfield

Stroll down Main Street to discover charming local shops and the historic Garden Theatre, where live performances still enchant audiences. Nearby, outdoor enthusiasts can hike the Poet's Seat Tower trail for panoramic views or paddle along the serene Deerfield River in neighbouring Deerfield.

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Top Greenfield Hotel Reviews

Courtyard by Marriott Hadley Amherst

10/10 Excellent

"Clean and well-maintained"

Hampton Inn Brattleboro

8/10 Good

"Very clean. Good full breakfast."

Vikings Villages Resort

10/10 Excellent

"Viking Village was such a unique and enjoyable stay! It was impeccable, every detail (and there were a lot of very fine ones) was perfectly executed. Very comfortable, quiet, and felt much more luxurious than we are used to as budget travelers. Every amenity was quality and in working condition, we especially appreciated the fireplace. Beautiful scenery and wildlife. No notes, everything was perfect!"

Comfort Inn & Suites Hadley - Amherst

10/10 Excellent

"Very well maintained hotel. The breakfast was great with many options to choose from."

Hotel UMass

8/10 Good

"Most convenient facility for any stays related to UMass Amherst. The underground parking facility is a bit dated and unappealing but the facility is quite good otherwise"

Hotel Northampton

10/10 Excellent

"Well maintained rooms in this historic hotel. Located in downtown Northampton in the middle of all the restaurants, music venues and boutique stores. Friendly staff and two restaurants and a bar on site. Henry"

Hampton Inn & Suites Greenfield

8/10 Good

"Basic room. Felt a little dated. Breakfast was amazing."

Windmill Motel Restaurant

10/10 Excellent

"Beautifully restored. Modern electronics, including security."

Colonial Motel

8/10 Good

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More cheap stays in Greenfield