Holiday Rentals in Greenfield, MA

20 available vacation rental offers

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Greenfield, MA holiday rentals
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Best Holiday rentals and Airbnb offers in Greenfield, MA

Explore Holiday Rentals for Families in Greenfield, MA

Choosing a holiday rental built for families in Greenfield, MA means city attractions are close by for a much smoother trip.

The Mountain House - Greenfield, MA
9.7 22 reviews
Greenfield, MA
15/07 – 20/07
£348/nightTotal: Â£1740 (5 )

The Mountain House

4 2
apartment , Gill
This 4-bedroom family home sits atop Mount Pisgah, just 3.2 kilometres from the Mohawk Trail and 8 kilometres from Greenfield, offering stunning views and a tranquil setting in the heart of the Berkshire Hills. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The house is spacious and comfortably accommodates up to 8 guests, with a full kitchen, dining room, family room, and a nursery with a twin bed. Guests can enjoy a private garden, parking, and access to the entire first and second floors, sunroom, breezeway, and attached garage, making it ideal for families and groups seeking a secluded escape in the beautiful surroundings.
The Jelly Mill-a Peaceful River Retreat - Greenfield, MA
9.9 209 reviews
Greenfield, MA
27/06 – 30/06
£211/nightTotal: Â£633 (3 )

The Jelly Mill-a Peaceful River Retreat

3 2
apartment , Guilford
This 3-bedroom cottage is situated on a quiet dirt road in Guilford, Vermont, just 20 kilometres from Brattleboro, where you'll find shops, restaurants and petrol stations. It has received excellent ratings for its location, cleanliness and overall experience.
The 121-square-metre property can comfortably accommodate up to 6 guests. The cottage boasts a fully equipped kitchen, a private garden with a picnic table and barbecue, a converted garage with a patio, a Roku device for streaming, and a selection of books and games, ensuring plenty of entertainment options.
Rose Wisteria 4 Guests 2 Bedrooms-full+queen Beds - Greenfield, MA
Greenfield, MA
15/07 – 20/07
£220/nightTotal: Â£1100 (5 )

Rose Wisteria 4 Guests 2 Bedrooms-full+queen Beds

2 2
apartment , Shelburne
This two-bedroom flat in Shelburne Falls offers convenient access to local attractions, situated within walking distance of Glacial Potholes, Shelburne Falls, and the Bridge of Flowers, with free on-site parking.
This pet-friendly accommodation provides air conditioning and a fully equipped kitchen for up to four guests, with on-site kayaking activities and proximity to cultural sites such as the White Barn Studio and Charlemont Historical Society and Museum.
On-the-river Retreat - Greenfield, MA
9.7 6 reviews
Greenfield, MA
25/07 – 27/07
£194/nightTotal: Â£388 (2 )

On-the-river Retreat

1 3
apartment , Buckland
This apartment in Shelburne Falls village offers direct riverside access, ideal for swimming, canoeing, and kayaking, and is a short walk to the Bridge of Flowers and local amenities including restaurants and shops.
This family-friendly flat sleeps up to six guests and features air conditioning, a kitchenette with a fridge, freezer, and microwave, a garden, and an outdoor patio with a firepit, with Berkshire East ski resort just a short drive away.

Choose the Right Self-Catering Holiday Rentals with Free Parking in Greenfield, MA

A car park at your holiday rental in Greenfield, MA means exploring the city centre is easy every day with no extra faff. Find your perfect stay.

Vikings Villages Resort - Greenfield, MA
Greenfield, MA
15/07 – 20/07
£211/nightTotal: Â£1055 (5 )

Vikings Villages Resort

1 2
resort , Guilford
The Vikings Villages Resort, offering the Vikings Villages Resort package, is situated in Jacksonville, 18 kilometres from Guilford city centre.
This self-contained accommodation provides WiFi, air conditioning, a terrace, garden, parking, and an elevator, with a picnic area for guests' enjoyment.
Deck, Mountain Views Colorful Retreat In Vernon! - Greenfield, MA
10 5 reviews
Greenfield, MA
25/07 – 27/07
£181/nightTotal: Â£362 (2 )

Deck, Mountain Views Colorful Retreat In Vernon!

2 3
apartment , Vernon
This Vernon apartment, situated 16 kilometres from Fort Dummer State Park, offers easy access to Santa's Land USA (40 kilometres) and Molly Stark State Park (42 kilometres).
The 156-square-metre property boasts a spacious two-bedroom layout, sleeping up to 11 guests, and includes a fully equipped kitchen, free Wi-Fi, parking, and air conditioning.
Modern Farmhouse Close To Montague Retreat Center - Greenfield, MA
9.9 194 reviews
Greenfield, MA
25/07 – 27/07
£405/nightTotal: Â£810 (2 )

Modern Farmhouse Close To Montague Retreat Center

1 3
apartment , Montague
This restored farmhouse, situated in the picturesque Montague, Massachusetts, is just 8 kilometres from the Montague Retreat Centre and a 32-kilometre drive from Northampton.
This spacious property, perfect for families, boasts three bedrooms, two bathrooms, and can comfortably accommodate up to eight guests, featuring modern amenities such as a dishwasher, air conditioning, and a dedicated play area for children.
Rustic-chic Cottage With Yard And Grill - Near Hiking! - Greenfield, MA
9.7 35 reviews
Greenfield, MA
27/06 – 30/06
£150/nightTotal: Â£450 (3 )

Rustic-chic Cottage With Yard And Grill - Near Hiking!

2 2
house , Northfield
The Rustic-Chic Cottage is located in Northfield, just 39 kilometres from both Amherst College and the Beneski Museum of Natural History, making it a great base for exploring the area. The cottage has received excellent ratings for user experience, location, and cleanliness.
This 2-bedroom cottage sleeps 2 guests and offers 125 square metres of living space. The cottage is fully equipped with a kitchen, air conditioning, free Wi-Fi, a garden, and free bikes, plus it has a patio with river views and is close to hiking trails.

Frequently asked questions about holiday rentals in Greenfield, MA

  • When is the best time to book a vacation rental in Greenfield, MA?

    The best time to book a vacation rental in Greenfield is in the spring or autumn. The weather is mild, and there are fewer crowds. You can find great deals on rentals during these seasons.
  • What are the best Airbnb and holiday rentals in Greenfield, MA?

    Mohawk Trail View/ Private Apt - No Cleaning Fee, Lovely 2nd Floor Apartment and The Cozy Treetop Apartment are among the best Airbnb and holiday rentals in Greenfield, MA.

  • What are the best budget-friendly activities in Greenfield, MA?

    A stroll along the Greenfield Bikeway is a great way to enjoy the scenery and get some exercise. The Greenfield Public Library is a free resource with a great collection of books and movies. The Greenfield Community College campus also has a number of free events throughout the year.
  • What are the most popular Airbnbs in Greenfield, MA?

    Among the Airbnbs in Greenfield, MA, Mohawk Trail View/ Private Apt - No Cleaning Fee, The Cozy Treetop Apartment and Lovely 2nd Floor Apartment are the most popular ones.

  • Are there pet-friendly attractions in Greenfield, MA?

    The Greenfield Town Common is a great place to take your dog for a walk. The Greenfield Farmers' Market also allows dogs on leashes. The Greenfield Community College campus is also a great place for a walk with your dog, as it has a number of open spaces and trails.
  • What are the best rentals for families and kids in Greenfield, MA?

    The best rentals for families and kids in Greenfield, MA are Lovely 2nd Floor Apartment, Cozy Farmhouse Apartment and Treehouse Retreat.

  • What are the top sports attractions and facilities in Greenfield, MA?

    Greenfield is home to the Greenfield High School, which has a number of sports teams, including football, basketball, and soccer. The Greenfield Community College also has a number of sports teams, including baseball, softball, and volleyball. There are also a number of parks and recreation facilities in the area, including the Greenfield Town Common, which has a playground, a basketball court, and a tennis court.

Destinations nearby

Best Self-Catering Holiday Rentals with a Terrace in Greenfield, MA

Enjoying morning coffee with city skyline views is a simple pleasure when staying in these holiday rentals and Airbnbs in Greenfield, MA.

Vikings Villages Resort - Greenfield, MA
Greenfield, MA
15/07 – 20/07
£211/nightTotal: Â£1055 (5 )

Vikings Villages Resort

1 2
resort , Guilford
The Vikings Villages Resort, offering the Vikings Villages Resort package, is situated in Jacksonville, 18 kilometres from Guilford city centre.
This self-contained accommodation provides WiFi, air conditioning, a terrace, garden, parking, and an elevator, with a picnic area for guests' enjoyment.
Charming 1-br Apartment In Conway, Wifi/ac - Greenfield, MA
10 3 reviews
Greenfield, MA
25/07 – 27/07
£143/nightTotal: Â£286 (2 )

Charming 1-br Apartment In Conway, Wifi/ac

1 3
apartment , Conway
This spacious one-bedroom apartment in Conway, Massachusetts, is situated in a historic Victorian mansion dating back to the 1880s, a 16-kilometre drive from I-91 and approximately 32-40 kilometres from Greenfield, Amherst, Northampton, and Berkshire East.
The self-catering flat, sleeping up to six guests, boasts vintage features including marble fireplaces, high ceilings, and a unique ‘wildscaped’ yard with a pond; laundry facilities are available by arrangement, and high-speed internet access is provided.

Popular Pet-Friendly Holiday Rentals in Greenfield, MA

Bringing your dog to Greenfield, MA? These holiday rentals are perfectly set up with dog parks nearby and city walks on the doorstep.

Shelburne Falls House In Village - Greenfield, MA
10 4 reviews
Greenfield, MA
25/07 – 27/07
£447/nightTotal: Â£894 (2 )

Shelburne Falls House In Village

1 3
apartment , Shelburne
This immaculate Victorian house in Shelburne Falls offers a peaceful retreat, a short walk from the village centre with its shops, restaurants, and bowling alley.
The three-bedroom property, sleeping six, features an open-plan kitchen-family room, a dining room, and a private back deck with a barbecue, plus garage storage for sports equipment; nearby activities include skiing, cycling, and rafting.
Wood Turtle Woods - Greenfield, MA
10 34 reviews
Greenfield, MA
25/07 – 27/07
£226/nightTotal: Â£452 (2 )

Wood Turtle Woods

1 3
farm , Conway
Wood Turtle Woods, a converted barn in Western Massachusetts, offers a tranquil escape 40km from Northampton, Greenfield, and Berkshire East Mountain Resort.
This one-bedroom property sleeps four, boasting two bathrooms, a fully equipped kitchen including a freezer, microwave, and dishwasher, plus Wi-Fi, air conditioning, parking, and a garden; nearby activities include hiking, cross-country skiing, and exploring local breweries.
Rustic Beauty: 2-bedroom House In Serene Shelburne Falls - Greenfield, MA
Greenfield, MA
25/07 – 27/07
£405/nightTotal: Â£810 (2 )

Rustic Beauty: 2-bedroom House In Serene Shelburne Falls

2 3
apartment , Shelburne
This 2-bedroom, 2-bathroom apartment in Shelburne offers expansive valley views towards the Seven Sisters range, located just 5 minutes from the I-91 and close to local landmarks such as Old Greenfield Village and the Bridge of Flowers.
This property accommodates up to 4 guests and features a well-equipped kitchen, a dedicated Family Office with a crib, a Yoga Room, and a main bathroom with a deep soaking tub, all set within spacious outdoor areas perfect for recreation.
Family Home | Flexible Layout | Walkable Town - Greenfield, MA
9.7 98 reviews
Greenfield, MA
15/07 – 20/07
£242/nightTotal: Â£1210 (5 )

Family Home | Flexible Layout | Walkable Town

1 2
apartment , Greenfield Town
This Greenfield family home, centrally located on a main street yet set back from the road, offers easy access to Deerfield Academy, Northfield Mount Hermon, and the Five Colleges.
The four-bedroom, one-bathroom property sleeps five guests and boasts a private balcony with hammock, Goshen stone patio, and high-end amenities including a dishwasher, microwave, fridge and freezer, plus Wi-Fi and air conditioning; regular professional cleaning is available for longer stays (at extra cost).
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