We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Westfield, MA and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Price
    per night
    |||
    |||
    $0
    $249 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Don't let other travelers get your favorite Westfield area vacation rental. You're so close to securing your perfect getaway. Book today.

    The following rentals are within 25 miles of Westfield, Massachusetts.

    Becket
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    other travelers have booked this property
    From
    $195
    / Night
    Payment Protection
    View Details
    View Details
    1 / 15
    5 of 5 stars (2) Excellent
    Sandisfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
    From
    $1,250
    / Week
    Payment Protection
    View Details
    View Details
    1 / 18
    5 of 5 stars (10) Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other travelers have booked this property
    From
    $1,395
    / Week
    Payment Protection
    View Details
    View Details
    1 / 11
    Becket
    6 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
    From
    $325
    / Night
    View Details
    View Details
    Amenities & Details
    • Grill
    • Porch
    • Patio
    • Internet Access
    • Parking
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds.... View all property information
    Location Information
    Becket, Berkshires 01223
    1 / 13
    5 of 5 stars (8) Excellent
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travelers have booked this property
    From
    $119
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful,... View all property information
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed November 3, 2014
    This was exactly what we were looking for in a getaway rental! The place was exactly as described and every bit of the transaction went by without a hitch. The house was cozy...
    5 of 5 stars Reviewed June 28, 2014
    The Becket cabin is a great getaway for young families. Our 4- and 2-year-old happily played about in and around the cabin and we spent a lot of time building fires in the fire...
    See all reviews
    Barkhamsted, CT
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
    other traveler has booked this property
    From
    $695
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Grill
    • Waterfront
    • Patio
    • Porch
    • Satellite TV
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nestled on the banks of the Farmington River, Legends offers comfortable rooms in a lodge setting with river views, breakfast Thursday -Sunday, healthy afternoon snacks and a special homemade juice of the day. All rooms offer AC, private bath, TV and internet. Fly-fishing,hunting kayaking, hiking,... View all property information
    Location Information
    Barkhamsted, Connecticut 06063
    1 / 32
    5 of 5 stars (2) Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    From
    $275
    / Night
    Payment Protection
    View Details
    View Details
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our... View all property information
    Location Information
    Becket, Berkshires 01223
    5 of 5 stars Reviewed August 18, 2015
    Amazing place for its location, layout, and superb owner! 1. The location is ideal. It's under 3 miles to Jacobs Pillow Dance, about 25 minutes to Tanglewood, 12 minutes form...
    5 of 5 stars Reviewed August 29, 2014
    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents...
    See all reviews
    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $225
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Porch
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, WiFi and cable included, and... View all property information
    Location Information
    Hatfield, Hampshire County 01038
    1 / 16
    Becket
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
    From
    $300
    / Night
    View Details
    View Details
    Amenities & Details
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional... View all property information
    Location Information
    Becket, Berkshires 01223
    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveler has booked this property
    From
    $200
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, WiFi and cable included, and... View all property information
    Location Information
    Hatfield, Hampshire County 01038
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    Belchertown
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    From
    $400
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This beautiful turn-of-the-century Victorian is the former rectory to a beautiful old church that is now an artist studio (The Artist Common - available for rent separately). It is secluded a top a hill on 4 1/2 acres and has soaring ceilings, period details, modern kitchen and 2 1/2 bathrooms. You... View all property information
    Location Information
    Belchertown, Hampshire County 01007
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 2 | Quick View
    From
    $850
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Private Yard
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water... View all property information
    Location Information
    Becket, Berkshires 01223
    Otis
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    other traveler has booked this property
    From
    $500
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    THIS IS A FULLY FURNISHED LARGE RETREAT IN THE HEART OF THE BERKSHIRES...SKIIING, LAKES, ANTIQUES, CRAFT SHOWS, ARTS, THEATRE ALL NEAR BY.....HOME IS IN A PRIVATE COMMUNITY WITH ITS OWN LAKE, POOLS, STATE OF THE ART FITNESS CENTER, CLUBHOUSE, HIKING TRAILS, TENNIS AND MORE! ONLY 2 1/2 HRS FROM NY... View all property information
    Location Information
    Otis, Berkshires 01255
    Springfield
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $4,200
    / Week
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Patio
    • Air Conditioning
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Spacious house, with hardwood floors and screened-in porch. View all property information
    Location Information
    Springfield, Massachusetts 01104
    1 / 31
    5 of 5 stars (1) Excellent
    Simsbury, CT
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    other travelers have booked this property
    From
    $350
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Terrace
    • Washer
    • Balcony
    • Parking
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Near SKI SUNDOWN ~ New Nantucket Style Home ~ Spacious NEW 4 Bedroom, home, French Doors Galore! Light Bright & Open! Large Gourmet Kitchen, Nice Deck for relaxing! Situated on 4+ private acres, in a park like setting. Master suite + 1st floor bedroom suite. Private yet convenient getaway!Our... View all property information
    Location Information
    Simsbury, Connecticut 06070
    5 of 5 stars Reviewed July 7, 2015
    My three friends and I (two couples) are from NYC and found this place in search of a July 4th weekend getaway. The house itself is gorgeous and very spacious (at least compared...
    See all reviews
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $189
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Light, airy, tasteful, contemporary and comfortable 5 room apartment with kitchen, dining room, living room with fireplace, den/study, bedroom with queen size platform bed. Bathroom has claw foot tub for showers or bath. Private garage bay. Keyless apartment entry. Ten minute walk to downtown... View all property information
    Location Information
    Northampton, Hampshire County 01060
    Northampton
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $350
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Patio
    • Grill
    • Parking
    • Porch
    • Washer
    • Air Conditioning
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful in-town single family home for weekly or extended rental in Northampton's tranquil Smith College neighborhood. 3 Bedroom, 1.5 bath. Max 6. Great for walking the home is close to town, easy to find, and on a very nice street in a gorgeous part of town. This New England home has original... View all property information
    Location Information
    Northampton, Hampshire County 01060
    1 / 42
    Avon, CT
    Studio, 1 Bathroom, Sleeps 4 | Quick View
    From
    $99
    / Night
    View Details
    View Details
    Amenities & Details
    • Hot Tub
    • Shared Outdoor Pool...
    • Internet Access
    • Air Conditioning
    • Parking
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Experience high-end amenities and upscale accommodations in this Avon vacation rental, with direct access to the Beaver Creek Gondola and views of the pool from your own private balcony. Located in the heart of Avon, this resort complex includes a gondola to the base of Beaver Creek's Lift 15,... View all property information
    Location Information
    Avon, Connecticut 81620
    East Longmeadow
    2 Bedrooms, Sleeps 2 | Quick View
    From
    $10
    / Night
    Payment Protection
    View Details
    View Details
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street House Main Street... View all property information
    Location Information
    East Longmeadow, Massachusetts 01028
    Bloomfield, CT
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $65
    / Night
    Payment Protection
    View Details
    View Details
    Amenities & Details
    • Wi-Fi
    • Central Heating
    • Washer
    • Porch
    • Parking
    • Private Yard
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nice get away. Come see our hard wood floors in the living rm, bedrooms (2), with bath & Eat- in kitchen and enjoy your own washer & dryer Hook-Up and storage areas in your own basement. These units are equipped with OIL Heat, Electric hot water and stove. A must see with All Utilities are... View all property information
    Location Information
    Bloomfield, Connecticut 06002
    Get the List
    1 / 24
    Barkhamsted, CT
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
    From
    $215
    / Night
    View Details
    View Details
    Amenities & Details
    • Waterfront
    • Washer
    • Internet Access
    • Balcony
    • Grill
    • DVD Player
    • Central Heating
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This turn-of-the-century, family. year round lake lodge is in the township of Barkhamsted, Connecticut. It is in the foothills of the Berkshires, nestled at the northwest bank of Connecticut's clearest lake, West Hill Lake. The owner retained the nostalgic feel of a comfortable antique lake home... View all property information
    Location Information
    Barkhamsted, Connecticut 06063