Holiday Rentals in Greenfield, MA

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

Search Holiday Rentals near the Heart of the City in Greenfield, MA

Book self-catering holiday rentals for couples in Greenfield, MA to enjoy private, intimate dining spaces during your city break.

Light-filled Treetop Apartment Close To Downtown Greenfield And Highland Park - Greenfield, MA
10 12 reviews

Light-filled Treetop Apartment Close To Downtown Greenfield And Highland Park

apartment, Greenfield Town
This one-bedroom flat is located within a historic Victorian mansion in Greenfield, just a few blocks from the town centre, offering a secluded natural retreat surrounded by mature pines and close to the Connecticut River trails.
This pet-friendly apartment accommodates up to four guests and features a microwave, dishwasher, air conditioning, a private terrace or balcony, and access to a zen garden, with nearby attractions including Griswold Wildlife Sanctuary and Richardson's Candy Kitchen.
Cozy 2-bedroom Apt - Greenfield, MA
9.6 56 reviews

Cozy 2-bedroom Apt

apartment, Greenfield Town
This Greenfield Town apartment, a first-floor flat near the town centre, is conveniently located across the road from a skate park.
The two-bedroom dwelling, sleeping up to six guests, offers a fully equipped kitchen with dishwasher, in-unit laundry, and a living area with a flat-screen TV; note that noise from upstairs neighbours may be audible.
Family Home | Flexible Layout | Walkable Town - Greenfield, MA
9.7 108 reviews

Family Home | Flexible Layout | Walkable Town

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).
Treetop Haven - Greenfield, MA
9.8 44 reviews

Treetop Haven

apartment, Greenfield Town
This one-bedroom flat is located a few blocks from Greenfield town centre, atop a hill within a historic Victorian mansion, offering a tranquil escape.
Guests can enjoy a secluded setting with access to a zen garden, meditation bench, and trails leading to Highland Park and the Connecticut River, with an internet connection and air conditioning provided.

Best Greenfield, MA holiday rentals with air conditioning

Downtown Modern Apartment - Greenfield, MA
10 85 reviews

Downtown Modern Apartment

apartment, Shelburne
This apartment is situated on Bridge Street in Shelburne Falls, a short walk from the iconic Shelburne Falls Bridge of Flowers and the town centre's shops and restaurants.
The apartment, which occupies the entire second floor of a historic brick building, offers comfortable accommodation for up to six guests and features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning and parking.
Spacious Contemporary Near Hiking Trails, Downtown - Greenfield, MA
10 2 reviews

Spacious Contemporary Near Hiking Trails, Downtown

apartment, Greenfield Town
This contemporary dwelling is located in Greenfield's Highland Park district, offering walking access to downtown Greenfield and direct proximity to Temple Woods hiking trails.
This 3-bedroom, 2-bathroom residence accommodates up to 7 guests, featuring a private swimming pool, air conditioning, and a dedicated office space, with nearby clay tennis courts for recreation.
Flowers & Falls Spot House - Greenfield, MA
9.8 52 reviews

Flowers & Falls Spot House

apartment, Buckland
This two-bedroom apartment in Buckland is situated just 15 kilometres from Berkshire East Mountain Resort, overlooking the Salmon Falls and Bridge of Flowers. The apartment has been given excellent ratings for location, cleanliness and user experience.
The apartment offers a comfortable stay for up to six guests, with one bathroom and a fully equipped kitchen. Guests can enjoy a private garden, parking, air conditioning and breathtaking views from the outdoor deck.
Frimpong's Two Bedroom Apartment - Greenfield, MA
9.5 87 reviews

Frimpong's Two Bedroom Apartment

apartment, Montague
This basement flat is located in the Lake Pleasant neighbourhood of Montague, just a two-minute walk from the lake and within easy reach of neighbouring towns like Greenfield, Sunderland, and Northampton. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
The self-catering flat has two bedrooms and one bathroom, comfortably accommodating up to three guests. The property offers a private entrance, a kitchenette, a modern and fully furnished interior, a TV with Wi-Fi access, air conditioning, and parking.

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.

Popular destinations

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.

Cozy Mountain Retreat-25 Secluded Acres-beautiful Foliage Views!   Dog Friendly! - Greenfield, MA
9.8 125 reviews

Cozy Mountain Retreat-25 Secluded Acres-beautiful Foliage Views! Dog Friendly!

cabin, Halifax
This Halifax mountain property is located within 15km of Jacksonville Pond, Harriman Reservoir, Deerfield River, The Ledge, and Honora Winery, offering easy access to outdoor activities and sightseeing.
This 186 square metre house sleeps eight guests in three bedrooms and two bathrooms, boasting a fully equipped kitchen, jacuzzi, spa, terrace, garden, parking, and free Wi-Fi.

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.

Charming Brookside Artisan Home - Greenfield, MA
10 125 reviews

Charming Brookside Artisan Home

apartment, Shelburne
This peaceful country house is located 10km from Greenfield and the village of Shelburne Falls, and 30km from the five college area, offering a tranquil escape from city life. The property has received excellent ratings for location, cleanliness, and overall experience.
The house has three bedrooms and one bathroom, accommodating up to six guests. It features a well-equipped kitchen, a wraparound porch, and dedicated workspaces with high-speed Wi-Fi, perfect for families or groups seeking a comfortable and spacious retreat.
1770 House - An End Of A Dirt Road Hideaway Where You Can Relax And Unwind. - Greenfield, MA
10 7 reviews

1770 House - An End Of A Dirt Road Hideaway Where You Can Relax And Unwind.

apartment, Colrain
This spacious Colrain holiday home, boasting 418 square metres of floor area, is situated approximately 10 kilometres from the Green River Wildlife Management Area, Greenfield Beach, Eunice Williams Covered Bridge, and Griswold Memorial Library.
This six-bedroom, three-bathroom property sleeps twelve guests and offers a swimming pool, hot tub, terrace, garden, parking, and a fully equipped kitchen including a dishwasher, alongside charcoal grills and excellent user reviews.
The Mountain House - Greenfield, MA
9.6 27 reviews

The Mountain House

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.
Ideal Family Skiing, Snow! Xmas Village Charm - Greenfield, MA
9.5 63 reviews

Ideal Family Skiing, Snow! Xmas Village Charm

apartment, Buckland
This charming seven-bedroom house is located in the heart of Buckland, a picturesque New England village, just a two-minute walk from the village centre and a five-minute walk from the river and the Bridge of Flowers. The property has received excellent ratings for location, cleanliness, and overall user experience.
The spacious home comfortably accommodates up to 14 guests and features a well-equipped kitchen, dining/living area, two sitting rooms, a playroom, a wood stove, cable TV, and wireless internet. Guests can enjoy a private garden, parking, and a range of activities, including swimming, river rafting, hiking, skiing, and zip-lining.

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.

Amazing Country Getaway / Buckland Retreat House - Greenfield, MA
9.9 129 reviews

Amazing Country Getaway / Buckland Retreat House

apartment, Buckland
Charming 3-bedroom Family Retreat, Downtown Shelburne Falls. Walk To Everything! - Greenfield, MA
10 4 reviews

Charming 3-bedroom Family Retreat, Downtown Shelburne Falls. Walk To Everything!

apartment, Buckland
Charming 4 Bdrm House With Views, 200 Acres, Private Schools, Skiing, Hiking - Greenfield, MA
10 8 reviews

Charming 4 Bdrm House With Views, 200 Acres, Private Schools, Skiing, Hiking

apartment, Leyden
Old Deerfield Treasure! - Greenfield, MA
10 22 reviews

Old Deerfield Treasure!

apartment, Deerfield

Check Out 5-Star Self-Catering Holiday Rentals in Greenfield, MA

A city-centre luxury holiday rental or Airbnb in Greenfield, MA sets the perfect tone for your stay. Expect 5-star comfort and quality throughout.

Sunny Downtown 2br, Near Bridge Of Flowers - Greenfield, MA
9.7 502 reviews

Sunny Downtown 2br, Near Bridge Of Flowers

apartment, Shelburne

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

Shelburne Falls House In Village

apartment, Shelburne
Cozy Country House In Conway - Greenfield, MA
10 10 reviews

Cozy Country House In Conway

apartment, Conway
Montague Meadows - Space For The Whole Family - Greenfield, MA
10 32 reviews

Montague Meadows - Space For The Whole Family

apartment, Montague
Apartment In Scenic Shelburne Falls - Greenfield, MA
10 25 reviews

Apartment In Scenic Shelburne Falls

apartment, Shelburne

Compare Holiday Rentals with a Pool in Greenfield, MA

Pool access at your holiday rental makes a proper swim in the heart of the city part of your daily routine in Greenfield, MA.

The 1770 House - Greenfield, MA
9.8 143 reviews

The 1770 House

apartment, Colrain
1770 House - An End Of A Dirt Road Hideaway Where You Can Relax And Unwind. - Greenfield, MA
10 7 reviews

1770 House - An End Of A Dirt Road Hideaway Where You Can Relax And Unwind.

apartment, Colrain
Spacious Contemporary Near Hiking Trails, Downtown - Greenfield, MA
10 2 reviews

Spacious Contemporary Near Hiking Trails, Downtown

apartment, Greenfield Town

Guest-Favourite Holiday Rentals with a Hot Tub in Greenfield, MA

Private hot tub access after a day in the city is one of those details that makes a trip to Greenfield, MA truly memorable.

The 1770 House - Greenfield, MA
9.8 143 reviews

The 1770 House

apartment, Colrain
1770 House - An End Of A Dirt Road Hideaway Where You Can Relax And Unwind. - Greenfield, MA
10 7 reviews

1770 House - An End Of A Dirt Road Hideaway Where You Can Relax And Unwind.

apartment, Colrain
Sweet 3-bedroom House With Ac In Beautiful Wendell, Ma - Greenfield, MA
No reviews

Sweet 3-bedroom House With Ac In Beautiful Wendell, Ma

apartment, Wendell
Charming 4 Bdrm House With Views, 200 Acres, Private Schools, Skiing, Hiking - Greenfield, MA
10 8 reviews

Charming 4 Bdrm House With Views, 200 Acres, Private Schools, Skiing, Hiking

apartment, Leyden
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