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Westfield Vacation Rentals

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    Don't let other travelers get your favorite Westfield area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Westfield
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    The following rentals are within 20 miles of Westfield.
    Short Walk to Lake, Peaceful Getaway, Scenic Views1 / 13
    (3)Excellent
    Granville
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Three-bedroom one-and-a-half bath ranch with lots of room inside and outside1 / 17
    (1)Excellent
    Granby, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Zen Urban Flat near Downtown Springfield1 / 13
    (1)Excellent
    Springfield
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The White Room has a single queen sized bed and a beautiful cherry desk built by your host, John. This room has its own bathroom (ensuite) with a shower, toilet, sink, and toiletries. Sitting at the desk, you will see the east pasture where the llamas like to sleep in the summer. The rear window...
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    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    East Otis
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Balcony
    • Hot Tub
    • Parking
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beautiful Berkshires. Watch the horses roam. Have a guided trail ride (additional fee) or have a camp fire only feet away from the horses. Within steps from your accommodations, enjoy the largest recreational lake in Massachusetts. Bring your boat or jetski. Or use our row boat. Go...
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    East Otis, Berkshires 01029
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Corner Cottage in 16 Acres Springfield1 / 8
    (1)Excellent
    East Longmeadow
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Secure Parking
    • Cable/satellite TV
    • Private Yard
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 14, 2017
    peaceful and good host we would stay again and recommend her place to anyone also close to any stores
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    About this property
    Corner Cottage. This is a private house. It is a house-share. There are 2 adults and 2 cats living in the home. My home is very bright and sunny. My place is close to family-friendly activities, nightlife, and public transport. You’ll love my place because it is quiet and because of the location....
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    Location Information
    East Longmeadow, Massachusetts 01128
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lavender Room, or Inside room as we often call it, is nestled inside the house, and is located off the kitchen. It is the largest of the three rooms and was recently painted a lovely 'amethyst' or rich lavender color. Its bathroom, while not in the room, is located directly across the private...
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    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Hatfield, Hampshire County 01038
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Windy Top Stone Cottage1 / 58
    (1)Excellent
    North Granby, CT
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Secure Parking
    • Patio
    • Wi-Fi
    • Mountain Views
    • Air Conditioning
    • Grill
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 7, 2018
    My wife and I arrived at Windy Top in the middle of a snowstorm. What a perfect place to be snowed in! The cottage was beautifully decorated for the season and our hosts, Ken...
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    About this property
    The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to “summer” in the early part of the 20th Century. The cottage was the place where the domestic staff stayed when...
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    Location Information
    North Granby, Connecticut 06060
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Actually, the Pink room is painted a lovely 'Santa Fe red' and is a mirror image to the White Room. The Pink room has a single queen sized bed, and its own bath in the room (ensuite) with a shower, toilet, freestanding sink, and toiletries. Sitting at the spinette (an antique desk that once housed...
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    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    West Springfield
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lily's Lodge is your Home away from Home in Western Massachusetts. We are located directly across the street from the Eastern States Exposition Fairgrounds, minutes from downtown Springfield and within 5-15 minute drive to area colleges, Basketball Hall of Fame, and Six Flags. We provide our...
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    Location Information
    West Springfield, Massachusetts 01089
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    Bloomfield, CT
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BEAUTIFUL 100% NEWLY renovated Victorian Mansion, on 3.5 acre private ESTATE., directly alongside the ELEGANT greens and fairways of the prestigious private TUMBLE BROOK COUNTRY CLUB. LARGE INGROUND SWIMMING POOL. Great GOLF COURSE views from every window. PRIVATE- AWAY FROM THE ROADS- Large,...
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    Location Information
    Bloomfield, Connecticut 06002
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Otis
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Otis, Berkshires 01255
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Hatfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    new condo with open floor plan and first floor master with view across the Connecticut River to Mount Holyoke. Quartz countertops and high end appliances make it a dream kitchen. Master bedroom has steam shower and soaking tub. Second floor has one single bedroom (with room for inflatable bed or...
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    Location Information
    Hatfield, Hampshire County 01038
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Huntington
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You and your travel companions will be stricken by colonial beauty as you cross the threshold into this Huntington vacation rental home. The 3-bedroom, 2-bathroom house was constructed in 1789 and still boasts many of the original furnishings, but now features all of the modern amenities you'd...
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    Location Information
    Huntington, Hampshire County 01050
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Colebrook, CT
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Private Yard
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to our tastefully decorated home in Colebrook - nestled in the woodlands, this two-acre retreat offers a tranquil escape for up to 6 people and is only a 5-minute drive from town. Curl up by the fire in the family room or grab a blanket and make some smores around the fire pit! Perfect for...
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    Colebrook, Connecticut 06021
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Otis
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the woods of East Otis, you’ll have a peaceful stay in the Berkshires at this cozy 2-bedroom, 1-bathroom vacation rental cabin. Comfortably accommodating up to 5 guests, this retreat is perfect for a memorable family vacation. With miles of hiking trails to explore and the Otis Reservoir...
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    Location Information
    Otis, Berkshires 01029
    Cabin - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    West Hartland, CT
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elevate your lakeside retreat at this 3-bedroom, 2-bathroom vacation rental home that has accommodations for 8 in Tolland. Dive into lakeside fun on your private dock and hop on a kayak or stand-up paddleboard for a day of exploring this peaceful lake. When you’re not at the lake, enjoy fabulous...
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    Location Information
    West Hartland, Connecticut 01034
    Cabin - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Agawam
    Studio, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visit Agawam in comfort when you stay at this cozy vacation rental studio that sleeps 5, only a few minutes drive south from Springfield! Complete with a well-equipped kitchen, a plush queen-sized bed and a cozy lounge area with a flat-screen cable TV, this studio is perfect for families and...
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    Location Information
    Agawam, Massachusetts 01001
    Condo/Apartment - 1 Bathroom, Sleeps 5
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    Westfield Flight and Weather Info
    Airports nearby (1)
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    BDL
    Bradley Intl Airport
    13.1 miles from Westfield
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