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Featured Cottages in Greenfield

The Clearing - Quiet - Close To Nature
Exterior

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (195)
"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "
The Clearing - Quiet - Close To Nature
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (53)
"Great place just need the fire place to be fixed asap, especially for the winter time"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Rare new Home on Lake Whitingham. Semi-priv beach
Exterior

Rare new Home on Lake Whitingham. Semi-priv beach

10.0 out of 10, Exceptional, (3)
"Very nice place."
Rare new Home on Lake Whitingham. Semi-priv beach
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Exterior

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Historic Home w/ Modern Updates on < 4 Acres
House (4 Bedrooms) | Interior

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Quaint Massachusetts Home w/ Yard & Grill!
House (2 Bedrooms) | Interior

Quaint Massachusetts Home w/ Yard & Grill!

3.0 star property
Quaint Massachusetts Home w/ Yard & Grill!
Charlemont Retreat on Chickley River w/ EV Charger
Interior

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Near Hiking & Skiing: Home in Wilmington!
House (3 Bedrooms) | Interior

Near Hiking & Skiing: Home in Wilmington!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Near Hiking & Skiing: Home in Wilmington!
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Interior

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Exterior

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

9.6 out of 10, Exceptional, (64)
"We enjoyed our stay in this cozy cabin on the ridge. The owners have great taste and they have thought of everything to make the stay pleasant. "
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Cozy Wilmington Home: 6 Mi to Mount Snow!
House (4 Bedrooms) | Interior

Cozy Wilmington Home: 6 Mi to Mount Snow!

3.0 star property
Cozy Wilmington Home: 6 Mi to Mount Snow!
Cavalier Cottage B&B
Exterior

Cavalier Cottage B&B

3.0 star property
9.0 out of 10, Wonderful, (2)
"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "
Cavalier Cottage B&B
Wilmington Vacation Rental Near Hiking and Skiing!
Terrace/patio

Wilmington Vacation Rental Near Hiking and Skiing!

3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Exterior

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Wilmington Retreat Near Trails, Skiing & Festivals
House (3 Bedrooms) | Interior

Wilmington Retreat Near Trails, Skiing & Festivals

3.0 star property
10.0 out of 10, Exceptional, (1)
"Would definitely recommend! House had an everything we would need. So comfy and cozy! "
Wilmington Retreat Near Trails, Skiing & Festivals
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
House (1 Bedroom) | Front of property

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
House (2 Bedrooms) | Interior

Peaceful Marlboro Vacation Rental w/ Sauna & Yard!

3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
'john's Farmhouse in Mount Snow' on 120 Acres!
House (5 Bedrooms) | Interior

'john's Farmhouse in Mount Snow' on 120 Acres!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. "
'john's Farmhouse in Mount Snow' on 120 Acres!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
House (2 Bedrooms) | Interior

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Jacksonville Cabin w/ Wraparound Deck & Views
House (3 Bedrooms) | Interior

Jacksonville Cabin w/ Wraparound Deck & Views

3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Greenfield Hotel Reviews

The Ellery

The Ellery

10/10 Excellent
"Wonderfully convenient--I could park once, leave my car for the duration of my stay and daily walk to where I was working, as well as coffee houses/restaurants. I was also glad for the small fridge in the room, as well as the availability of coffee/decaf. "
Sarah 1-night trip
Posted 3 days ago
The Ellery

Frequently asked questions

What is there to do in Greenfield near my cottage?
The perfect travel accessory is a well-planned to-do list. Greenfield Beach is a great place to begin your exploration of Greenfield.