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
A bright living space features large windows, allowing natural light to fill the room. A comfortable sofa sits beside a wooden coffee table, with visible mountain views outside. A round dining table is surrounded by wooden chairs, enhancing the room's spacious feel.
Apartment in Shelburne Falls
4.92 out of 5 average rating, 291 reviews

Sunny, soaring 2-level downtown loft, scenic views

Walk to everything from this sunny, spacious 2-level, newly renovated 3rd-floor loft in downtown Shelburne Falls, right by the Bridge of Flowers. Cathedral ceiling, giant windows with views of mountains & river. Open upstairs queen bed space. Comfy pull-out queen bed downstairs. Washer/dryer. Well-equipped kitchen w/ dishwasher. Brand-new tiled shower. Fast Internet, two smart TVs, and a 15,000 BTU air conditioner that cools the big space in minutes. 15-minute drive to Berkshire East ski resort.

Top guest favorite
A two-story building is shown, featuring a red exterior complemented by a wooden deck with railings. Stairs lead up to the deck entrance. A green vehicle is parked nearby, with trash and recycling bins on the side. Leafless trees provide a backdrop.
Apartment in Williamsburg
4.96 out of 5 average rating, 138 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 Greek Revival farmhouse features a covered porch adorned with ferns and surrounded by lush greenery. The exterior showcases dark shutters and light green siding, framed by trees that provide shade and tranquility.
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
The exterior of a charming studio is showcased, featuring a low stone façade and a modern art sculpture in front of the lush green lawn. Solar panels are visible on the roof, and colorful decor accents the windows.
Guest suite in Greenfield
4.95 out of 5 average rating, 222 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
Apartment in Shelburne Falls
4.97 out of 5 average rating, 385 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.”

Guest favorite
A well-lit guest suite features a queen-sized bed with quality linens, positioned against a wall. A cozy day bed offers additional sleeping space. A round table and chairs complement the room, while large windows allow natural light to fill the space. A patterned area rug adds warmth.
Guest suite in Montague
4.91 out of 5 average rating, 244 reviews

Great Falls Private Suite

Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon. We are between downtown Turners Falls and Greenfield. If you're looking for a private and bright suite with beautiful natural light and a modern bohemian feel this is the space for you! Please note that there is a kitchenette but not a full kitchen. Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the CT River.

Top guest favorite
Apartment in Shelburne Falls
4.97 out of 5 average rating, 619 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Top guest favorite
Apartment in Greenfield
4.95 out of 5 average rating, 107 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
The garden features raised vegetable beds surrounded by a wooden fence. In the background, the charming former church building with a pointed steeple is visible, framed by vibrant autumn foliage in shades of red and orange.
Guest suite in Brattleboro
4.94 out of 5 average rating, 615 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

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
The exterior of the apartment is displayed, showcasing a light-colored siding with two dormer windows on the roof. A well-maintained lawn is visible, along with a white privacy fence surrounding the backyard area.
Apartment in Greenfield
4.96 out of 5 average rating, 471 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

Top guest favorite
The entrance features a wooden staircase leading to a covered porch with decorative columns. A red door serves as the focal point, complemented by large windows on either side that allow natural light to illuminate the area. Lush plants line the path, enhancing the inviting entrance.
Apartment in Greenfield
4.98 out of 5 average rating, 226 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. priceR2,813 ZARR2,813 ZARR2,813 ZARR2,942 ZARR3,006 ZARR2,942 ZARR2,942 ZARR2,958 ZARR2,894 ZARR2,974 ZARR2,974 ZARR2,958 ZAR
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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 R1,768 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!