Vacation rentals in Deerfield

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Top-rated vacation rentals in Deerfield

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

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Guest favorite
The open kitchen and living area features wooden cabinets and sleek appliances. Cozy yellow chairs and a coffee table are arranged in the seating area. A wall-mounted TV is visible, alongside a dining table with black chairs beneath large windows that allow natural light to fill the space.
Apartment in Shelburne Falls
4.87 out of 5 average rating, 485 reviews

Sunny downtown 2BR, near Bridge of Flowers

Urban 3-room (2 bdrm) apartment on 3rd floor of funky older apt building on the main street of Shelburne Falls. Apartment faces the street, with views of the hills beyond. New kitchen appliances, and newly remodeled bath with custom shower, tile floor, and washer/dryer. Interesting art throughout the apartment, including some original pieces. Steps to the Glacial Potholes, Bridge of Flowers; and all the galleries, shops, restaurants, and cafes that this charming New England village has to offer.

Top guest favorite
A serene pond reflects the white cottage and surrounding trees, creating a tranquil scene. Wildflowers and grasses frame the water's edge, while lush greenery enhances the natural beauty of the area. The peaceful environment is ideal for relaxation and outdoor exploration.
Cottage in Petersham
4.99 out of 5 average rating, 234 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Top guest favorite
The spacious studio apartment features a well-equipped kitchen with a countertop and bar seating. Natural light filters through the windows, highlighting wooden cabinetry and modern appliances. The open layout includes a cozy seating area, creating a functional living space beneath sloped ceilings.
Apartment in Williamsburg
4.96 out of 5 average rating, 143 reviews

The cozy clubhouse

Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.

Top guest favorite
A charming garden area is enclosed by a white picket fence, featuring an array of colorful flowers and tall sunflowers. The gray facade of the house provides a serene backdrop to the vibrant foliage, creating a welcoming atmosphere in the outdoor space.
Apartment in Conway
4.98 out of 5 average rating, 112 reviews

House Above the Hollow

A lovely peaceful spot set in the beautiful rolling hills of Conway Massachusetts, overlooking historic Pumpkin Hollow. In close proximity to Shelburne Falls, Deerfield, Greenfield, Amherst and Northampton along with the famed Tree House Brewery, just 10 min away. There are many sights, country roads, trails to explore, along with many varied restaurants to enjoy. "One of the most peaceful, scenic places I've ever stayed. You can really hear yourself think." Kathy Connolly Old Sabyrook CT.

Top guest favorite
A cozy studio bedroom features a spacious bed draped with a striped quilt, complemented by a decorative rug. Natural light enters through a window adorned with soft curtains. An art piece hangs above the bed, with a small table and two chairs accommodated nearby.
Guest suite in Greenfield
4.95 out of 5 average rating, 223 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

Top guest favorite
The kitchen features white cabinetry with black hardware and a tiled floor. An overhead fan circulates air. A round wooden table with placemats is set beside a lamp. Modern appliances, including a stove and microwave, are neatly integrated into the design.
Apartment in Shelburne Falls
4.97 out of 5 average rating, 386 reviews

Annies’ Place by The Bridge of Flowers ~

As a guest at Annie’s Place, enjoy access to a tastefully, renovated 3 room apartment, including a fully equipped kitchen, living room, sofa with 2 recliners, a spacious bedroom, ​walk-in closet, full bath, TV & Internet. There is a seasonal front porch and mudroom for convenience. Meticulously maintained and located in the downtown village area. Simply park and walk to specialty shops, restaurants & the Bridge of Flowers. Shelburne Falls, designated as one of the 15 “Great Places in America.”

Top guest favorite
Lush greenery surrounds a hidden garden feature, partially obscured by foliage. Various shades of green are complemented by clusters of small pink flowers, creating a natural and serene environment. The combination of plants provides a tranquil setting in the outdoor space.
Apartment in Village of Pelham
4.99 out of 5 average rating, 150 reviews

Pelham 2nd floor Apartment

Second floor newly finished apartment that accommodates 2 guest. Well water and septic. Green by recycling and using salvage materials. Environmentally benign materials used where possible. Solar. Utilities and internet included. Raspberries and blueberries in season. 3.9 miles from UMASS and Amherst Colleges. 5.3 miles from Hampshire College. 11 miles from Mt. Holyoke and 12 miles from Smith College. NO PETS ACCEPTED! Allergy free. Don't hesitate to contact us with questions!

Top guest favorite
A modern kitchen features white cabinetry and a spacious countertop. A white refrigerator and stove are positioned along one wall, while a round dining table set for two is placed in the foreground. Natural light brightens the room from an unseen window.
Apartment in Greenfield
4.95 out of 5 average rating, 108 reviews

Cozy one bedroom apartment

This is a beautiful one bedroom apartment located on the first floor that was recently remodeled. The stylish place is perfect for 2 people. It has a good size kitchen and a porch in the back. Located on a quiet and safe street yet close local restaurants and coffee shops. Easy hikes with great views like Poet Seat Tower and Highland Park. Also close to Deerfield Academy, Northfield Mount Hermon, The Bement School, Eaglebrook Schoool and Stonleigh-Burnham School.

Top guest favorite
A spacious, two-story dark wooden building is nestled among trees, showcasing a welcoming entrance with a large front porch. Lush green grass surrounds the structure, enhancing its serene setting. Bright blue skies and scattered clouds further complement the inviting atmosphere.
Apartment in Conway
4.96 out of 5 average rating, 209 reviews

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Top guest favorite
A well-maintained stone walkway leads to a private entrance, flanked by a wooden railing and a vibrant flower bed featuring red and yellow tulips. A white picket fence adds charm, while a BBQ grill is positioned nearby on a paved area.
Apartment in Greenfield
4.96 out of 5 average rating, 474 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Small, cozy private Apt is located in West Greenfield in a quiet, safe neighborhood. Guests have own private driveway and entrance. There are 2 TV’s, one in living room & bedroom. High speed internet. Queen size bed & desk. Apt. Is 2 min's to Rt. 2, Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes

Guest favorite
A classic log cabin stands surrounded by greenery, featuring a spacious front porch with a wooden railing. Large windows dominate the front, allowing natural light to fill the interior. An American flag is displayed, adding to the rustic charm of the structure.
Cabin in Plainfield
4.92 out of 5 average rating, 230 reviews

Peaceful Cabin in the Woods

Escape the noise and come relax in the middle of the beautiful Berkshire Hills. This classic log cabin has been recently renovated so that you can unwind and connect to the picturesque landscape that envelopes this property. You can drive 30 minutes west to North Adams and visit Mass Moca or 30 minutes east to Northampton, Amherst & Hadley. (Please note, 1/2 of the bedrooms is an open loft).

Top guest favorite
The living room features a comfortable sectional sofa and an armchair, paired with a round coffee table in the center. Large windows allow natural light to illuminate the space, complemented by indoor plants and light-colored walls.
Apartment in Greenfield
4.98 out of 5 average rating, 228 reviews

Lovely 2nd floor Apartment

This lovely spacious 1 bedroom apartment is situated on a quiet street in the heart of Greenfield. Only a 3 minute ride to a charming downtown & restaurants Enjoy lots of natural light and a calm office space with an additional futon for rest. Free parking on premises and access to nearby baseball field and tennis courts. A place you'll love to come back to.

Popular amenities for Deerfield vacation rentals

When is the best time to visit Deerfield?

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Avg. priceR2,861 ZARR2,861 ZARR2,861 ZARR2,992 ZARR3,057 ZARR2,992 ZARR2,992 ZARR3,008 ZARR2,943 ZARR3,025 ZARR3,025 ZARR3,008 ZAR
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Deerfield?

    Deerfield has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Deerfield?

    Experience the best of Deerfield with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there vacation rentals with a dedicated workspace in Deerfield?

    Yes! Work meets play with ease at over 10 vacation rentals in Deerfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Deerfield have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Deerfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Deerfield have a kitchen?

    Absolutely! We offer over 10 house rentals with a kitchen in Deerfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Deerfield have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Deerfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Deerfield have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Deerfield. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Deerfield?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Deerfield

  • Total vacation rentals

    Explore 20 vacation rentals in Deerfield

  • Nightly prices starting at

    Deerfield vacation rentals start at R1,799 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 1,760 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Deerfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Deerfield rentals

  • 5 Average rating

    Deerfield stays are highly rated by guests—averaging 5 out of 5!