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.
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.
Cozy 1br In Downtown Greenfield  Walk To Shops - Greenfield, MA
9.5 60 reviews

Cozy 1br In Downtown Greenfield Walk To Shops

apartment, Greenfield Town
This one-bedroom flat is situated centrally in Greenfield Town, a short walk from the Shea Theatre and the People's Pint restaurant, offering convenient access to local dining and entertainment.
This accommodation includes a king-sized bed, a fully equipped kitchen, air conditioning, and free off-street parking, providing a comfortable base for exploring the Berkshires and Mohawk Trail.
Charming Country-chic 1br In Greenfield  King Bed, Rain Shower, Near Berkshires - Greenfield, MA
9.6 9 reviews

Charming Country-chic 1br In Greenfield King Bed, Rain Shower, Near Berkshires

apartment, Greenfield Town
This one-bedroom flat in Greenfield, Massachusetts, offers direct access to downtown dining, the historic Shea Theatre, and the People's Pint brewery, with the Mohawk Trail and Berkshires accessible within 20 kilometres.
This serviced apartment accommodates up to four guests and includes a fully equipped kitchen, a king-size bed, an in-unit washer/dryer, and private off-street parking, with contactless check-in available through a key-coded entry.

Best Greenfield, MA holiday rentals with air conditioning

Shelburne Falls House In Village - Greenfield, MA
10 4 reviews

Shelburne Falls House In Village

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.
Mountaintop Views, Near Private Schools, Ski/golf - Greenfield, MA
10 38 reviews

Mountaintop Views, Near Private Schools, Ski/golf

apartment, Leyden
This secluded Leyden, Massachusetts chalet, situated 3.2km north of Greenfield and under 14.5km from Deerfield, its Academy, Eaglebrook School, and The Bement School, offers stunning mountaintop views and easy access to the Green River.
The 325m² newly renovated property boasts four bedrooms, three bathrooms, sleeping up to twelve guests, and features a large deck with a fire pit, a spacious kitchen, and an upcoming eight-person hot tub (completion end of November 2024); extensive trails are perfect for hiking and ATV riding.
Spacious & Cozy Ground Floor 2/3 Bed Private Suite - Greenfield, MA
9.5 12 reviews

Spacious & Cozy Ground Floor 2/3 Bed Private Suite

apartment, Shelburne
This Shelburne Falls apartment, a five-minute walk (0.8 km) from the town centre, offers easy access to Shelburne Falls' shops and restaurants.
Sleeping six guests comfortably, this three-bedroom, one-bathroom flat boasts a spacious layout including a living room, dining room, sunroom, well-equipped kitchen, and private south-facing garden with off-street parking.
Sunny, Shiny Downtown Flat W/mountain+river Views - Greenfield, MA
9.8 219 reviews

Sunny, Shiny Downtown Flat W/mountain+river Views

apartment, Shelburne
This apartment is in the historic district of Shelburne Falls, a short walk from the Bridge of Flowers and the town centre. It has excellent ratings for location, cleanliness, and user experience.
The apartment is on the top floor of a historic building, sleeping up to four guests. It has a fully equipped kitchen, a luxurious bathroom, and a comfortable living space with a queen-sized bed and a pull-out queen bed, plus a washer and dryer.

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.

Spacious 5br W/ Hot Tub & Games - Greenfield, MA
9.9 274 reviews

Spacious 5br W/ Hot Tub & Games

apartment, Colrain
This family-friendly property is located in Colrain, within a 5km radius of Arthur A. Smith Covered Bridge, G. William Pitt House and Collection, and White Barn Studio. It has received excellent ratings for its cleanliness, location, and overall user experience.
This 5-bedroom home spans 186 square metres and offers a range of amenities, including a fully equipped kitchen, a Jacuzzi, a terrace, and a garden. Guests can enjoy outdoor grilling, relax in the spa tub, and explore the nearby Deerfield River and High Ledges Wildlife Sanctuary.
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.

Shelburne Falls Combined Rental - Greenfield, MA
10 4 reviews

Shelburne Falls Combined Rental

apartment, Shelburne
This four-bedroom, two-bathroom house in Shelburne Falls, Massachusetts, sleeps eight and is ideally located for exploring the town's attractions, including the Bridge of Flowers (distance unspecified).
The property boasts a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, offering comfortable family accommodation with ample space.
The 1770 House - Greenfield, MA
9.8 143 reviews

The 1770 House

apartment, Colrain
This 1770 farmhouse is located in Colrain, Massachusetts, just a short drive from the Green River Valley and offering stunning views of Vermont. The property enjoys excellent ratings for location, cleanliness, and overall user experience.
This spacious country home sleeps up to 14 guests and offers a chef's kitchen, a large dining room with a huge hearth, a living room with original charm, and a double-decker deck with stunning views. The amenities include a private swimming pool and spa, an indoor cedar hot tub, high-speed internet, and a selection of toys for all ages.

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.

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

Sunny Downtown 2br, Near Bridge Of Flowers

apartment, Shelburne
Peaceful Cabin In The Woods And Near The Mountains - Greenfield, MA
10 10 reviews

Peaceful Cabin In The Woods And Near The Mountains

cabin, Halifax
The Nest
In Shelburne Falls - Greenfield, MA
No reviews

The Nest In Shelburne Falls

apartment, Shelburne
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

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.

Spacious 5br W/ Hot Tub & Games - Greenfield, MA
9.9 274 reviews

Spacious 5br W/ Hot Tub & Games

apartment, Colrain

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.

Mountaintop Views, Near Private Schools, Ski/golf - Greenfield, MA
10 38 reviews

Mountaintop Views, Near Private Schools, Ski/golf

apartment, Leyden
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
Charming Country-chic 1br In Greenfield  King Bed, Rain Shower, Near Berkshires - Greenfield, MA
9.6 9 reviews

Charming Country-chic 1br In Greenfield King Bed, Rain Shower, Near Berkshires

apartment, Greenfield Town
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

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.

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
The 1770 House - Greenfield, MA
9.8 143 reviews

The 1770 House

apartment, Colrain

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.

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
Spacious 5br W/ Hot Tub & Games - Greenfield, MA
9.9 274 reviews

Spacious 5br W/ Hot Tub & Games

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
The 1770 House - Greenfield, MA
9.8 143 reviews

The 1770 House

apartment, Colrain
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