Holiday rentals in Greenfield

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Top-rated holiday rentals in Greenfield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A cozy log cabin is set back from the road, surrounded by lush greenery and blooming flowers. A gently sloping driveway leads to a covered porch with seating, inviting guests to enjoy the natural surroundings and tranquil atmosphere.
Cabin in Greenfield Center
4.96 out of 5 average rating, 311 reviews

Cozy Log Cabin in the Woods

Scenic, cozy log cabin set back in the woods. Fully furnished & decorated. Full kitchen, 1.5 bath, washer/dryer. 1 bedroom w/full & twin bed. 1 room w/queen bed. 2 twin XL cots available. See pictures for bed dimensions. Handicap accessible, Desk area, Wifi, NO landline, good verizon signal,Roku tv, Heat & AC. Pets allowed. Owner lives above garage. Dogs live on property. Hens and roosters, are housed near the cabin, they can make noise day and night. Large front porch. Bring your slippers. :-)

Top guest favourite
Cabin in Shaftsbury
4.99 out of 5 average rating, 481 reviews

Vermont Dream Cabin~70 Acres w/Hot Tub & Fireplace

Log cabin w/ hot tub on 70 acres of Vermont forest with hiking/snowshoe trails, river & mountain stream. Cozy up with wine, games or book by the huge stone woodburning fireplace with fav music from the vintage Bose stereo, enjoy coffee & stargazing on the rocking porch while taking in the mountain views & wildlife or explore the forest & river trails. Enjoy making meals in the ample fully stocked kitchen, the outdoor grill & around the campfire. Crisp AC.*4x4/AWD a MUST for WINTER only BOOKINGS*

Top guest favourite
A historic Victorian mansion stands gracefully, showcasing intricate architectural details and multiple gabled roofs. A flowering tree adds a natural touch in the foreground, while soft lighting emanates from the windows, creating a welcoming ambiance in the evening.
Flat in Saratoga Springs
4.98 out of 5 average rating, 259 reviews

Saratoga Gem

This lovely apartment is on the second floor of an 1873 Victorian mansion on the North side of town. Very conveniently located about halfway between downtown and Skidmore College. This clean, quiet, owner-occupied house has 2 other apartments. The classic Saratoga front porch, sunny patio in back, and small yard are shared with the host. Kitchen has a small cafe table, dishes/utensils, dishwasher. Bathroom has a deep tub/shower, you’ll have to lift your knee to step in. Memory Foam mattress.

Top guest favourite
The cabin's exterior is characterized by warm wood siding and a gabled roof. A covered porch features two rustic chairs, inviting relaxation. Large windows flank the entrance, providing natural light. The surrounding landscape includes trees and a well-maintained lawn, enhancing the outdoor setting.
Cabin in Saratoga Springs
4.92 out of 5 average rating, 51 reviews

Three Bears Lodge of Saratoga

A beautiful cabin set on over two private acres less than 2 miles to Broadway, and exactly 4.4 miles to the track. Sit by the firepit, or relax in the hot tub, after a busy day of taking in the sights, dining, and everything else Saratoga has to offer. Large, 14 x 26, open bedroom upstairs with two authentic log queen size beds, rustic log furniture, a walk in closet, and log railings on the stairs. There's a full sized kitchen, full bath, laundry room, and a full size pull out sofa/sleeper.

Top guest favourite
A charming treehouse is nestled among lush green foliage, featuring a rustic wooden exterior and a wraparound deck. Sunlight filters through the trees, creating a serene atmosphere that invites relaxation and connection with nature.
Treehouse in Argyle
4.99 out of 5 average rating, 124 reviews

Out On a Limb • A Magical Treehouse Experience

Welcome to Out on a Limb, our magical treehouse nestled in the serene woods of upstate New York. This cozy, charming hideaway offers a peaceful & romantic escape, perfect for couples or solo travelers looking to connect with nature. Surrounded by towering trees, the treehouse provides a unique experience year round—from relaxing in the hot-tub on a snowy night, to stargazing by the campfire. The treehouse is always stocked with waffle mix & homemade frozen cookies. We can’t wait to host you!

Guest favourite
A well-appointed bedroom features a spacious bed with soft linens, accented by a decorative headboard. A cozy armchair and a small desk offer comfortable seating options. Natural light enters through a large window draped with light pink curtains, enhancing the relaxed atmosphere.
Home in Cropseyville
4.97 out of 5 average rating, 36 reviews

Grey House

Nestled in the beautiful hills of Grafton New York Greyhouse welcomes you. Grey house is a one story home that has been completely renovated with your comfort in mind. Adjacent to Greywacke Meadows. The 3 bedrooms are attractive and comfortable and sleep up-to six guests. Master bedroom has a private bathroom and a main bathroom is centrally located. Not wheelchair accessible at this time as there are stairs into the house. Multi level porches and a large patio with seating areas.

Top guest favourite
A rustic cottage is surrounded by lush greenery, featuring a wraparound deck made of wooden planks. Stone pathways and natural boulders are present, leading to the entryway. Two outdoor chairs are situated on the deck for relaxation amidst the tranquil forest setting.
Cottage in Middle Grove
4.98 out of 5 average rating, 126 reviews

Off Grid Cottage view of stream sitting on boulder

The Cottage at Brookledge former girls summer camp -11 mi. from Sacandaga Lake -12 mi. from downtown Saratoga + SPAC -Pet friendly -60 acres gated property -Firepit -View of stream with wrap around deck -Heat -Vintage cooler, no fridge -Cooktop, grill, kettle, pots, pans, utensils, dishes -Private outhouse -Showers in bathhouse (open year-round) -Water canister in cabin -Jackery generator for electricity -Games, books, hammock -No Wifi in cottage -Wi-Fi available in Pavilion

Guest favourite
A well-lit kitchen area is defined by its high ceiling and modern design. A red fridge stands out among neutral tones, while a spacious countertop with three wooden stools invites casual dining. Shelving displays plants and other decor, contributing to a welcoming atmosphere.
Home in Saratoga Springs
4.84 out of 5 average rating, 117 reviews

The Perfect Saratoga Cottage w/ Outdoor patio & TV

Live like a Local! Walk to everything from Broadway to Beekman Street Art District (less than a mile). Rent a bike or take a jog down the bike path to SPAC for live music, picnics and nature trails (about 1.5 miles). Summer Fun at the racetrack awaits less than 2 miles from the Historic Saratoga Race track! Enjoy a walk, bike or just take a UBER to the best place to be in the summer! All this is too much? Feel free to relax in the backyard completed with TV and firepit!

Top guest favourite
A cozy living area features a turquoise couch and a wooden coffee table. A small dining table is visible in the background, with a flat-screen television mounted on the wall. Natural light floods the space through large windows that overlook a private patio.
Flat in Saratoga Springs
4.99 out of 5 average rating, 95 reviews

Cozy charming one bedroom suite.

Have fun at this stylish setting. There is one bedroom, a large bathroom with tub, living room and kitchenette. Included is a futon which accommodates 2 smaller children or one adult. There is also a small private flagstone patio for nature lovers. It is located only 5 minutes from broadway, 8 minutes from SPAC and 10 minutes to Saratoga Racetrack. Lake George is a brief 30 minute drive. Unique to this location is a horse farm on the opposite side of the street.

Guest favourite
A charming treehouse is elevated among the lush foliage, featuring a rustic wooden exterior and a covered porch. Soft lighting enhances the inviting look, while a winding staircase leads to the entrance, surrounded by vibrant green trees.
Treehouse in Middle Grove
4.93 out of 5 average rating, 634 reviews

An Adirondack Tree House Retreat

Our treehouse is one of the most sought after places for couples to reconnect with nature. Nestled in the foothills of the Adirondack Mtns. and just 9 miles from Saratoga Springs NY, boasting quiet solitude. The winding staircase leads to a sleeping area and covered porch. Also, outdoor kitchen, deck, fire pit and full bath just a few steps away. Please keep in mind that our treehouse is meant as a quiet retreat for 1-3 people.

Top guest favourite
A cozy living area features a pair of brown leather sofas arranged around a wooden coffee table. A wall-mounted TV is above a shelf adorned with green plants and decorative items. Light-colored walls and hardwood floors enhance the welcoming ambiance.
Flat in Ballston Spa
4.95 out of 5 average rating, 160 reviews

Charming Country Setting

Newly remodeled, 1200 sq ft, 1st floor apartment in a charming country setting. Furnished with all the amenities of home. 10 ft ceilings, hardwood floors, and large TV. Fully stocked kitchen, bath, laundry, cable, WiFi, Located 4.5 miles west of Exit 12 of I-87, 12 miles to Saratoga with RACINO OR 20min. from RIVERS CASINO.Great venues surround us.

Guest favourite
Tiny home in Porter Corners
4.86 out of 5 average rating, 81 reviews

The Winslow

We invite you to the Winslow, meaning a friend's hill, nestled in the woods of a historic farm area. A tiny space, with lots of warmth and cozy vibes, this is a great landing spot for exploring upstate NY. Just 15 mins from all things Saratoga, 30 mins from Lake George, and a perfect day trip to Lake Placid.

Popular amenities for Greenfield holiday rentals