Holiday houses in Longmeadow

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Top-rated holiday rentals in Longmeadow

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Guest favourite

A cozy seating area is created by a sectional couch adorned with decorative pillows. A soft ottoman sits at the center on a plush area rug. Natural light enters through two windows, enhancing the comforting atmosphere of the space.

Home in Longmeadow

4.78 out of 5 average rating, 9 reviews

Cozy Cottage with fenced yard

Relax at this recently updated 2 BR cottage in peaceful Longmeadow w/ easy access to Rte 91 N & S. Visit Six Flags, Basketball Hall of Fame, Seuss Museum, Big E, Berkshires... Inside you'll find a sun filled, tastefully decorated home w/a comfy sectional couch, 2 smart TVs, electric fireplace, dining table for 4, well stocked kitchen w/ coffee station, & comfortable linens & towels. Outside enjoy the spacious private fenced backyard w/ deck, outdoor seating, & a gas grill. Pet friendly. Welcome!

Superhost

Home in Springfield

4.75 out of 5 average rating, 12 reviews

Safe & Quiet 3BR Cape: Sunroom Office + Yard

Welcome to The Allen Ridge Retreat. Tucked away in East Forest Park—Springfield’s most desirable and safest ("A" rated) neighborhood—this classic Cape Cod offers the peace of the suburbs with the pulse of the city just minutes away. Medical professionals seeking deep rest after a shift at Baystate, a family cheering on a WNEU grad, or explorers visiting The Big E, our home is your safe, and spotless sanctuary featuring gleaming hardwood floors, a dedicated sunroom office, and private backyard.

Guest favourite

A comfortable living room features a stylish sofa positioned against a brick wall, accented by large windows allowing natural light to brighten the space. A decorative coffee table rests on a vibrant area rug, while a plant adds a touch of greenery to the room.

Apartment in Springfield

5 out of 5 average rating, 25 reviews

The Smith Victorian | 2BR Brownstone Apartment

This beautifully preserved historic Victorian brownstone is ideally located within walking distance of many of downtown Springfield’s top attractions. The city’s museums are just one street away, with the Symphony Orchestra, dining, shopping, and MGM Springfield Casino nearby. Guests will enjoy on-street permit-only parking, electric baseboard heating, central air conditioning, a brand-new in-unit washer and dryer, high-speed internet, and a covered outdoor balcony perfect for morning coffee.

Top Guest favourite

A dining table is set with blue and white patterned bowls, layered on white plates. A floral placemat with muted colors is visible beneath. Fresh sunflowers are arranged in a glass vase, providing a natural touch to the inviting table setting.

Home in Longmeadow

4.95 out of 5 average rating, 20 reviews

Great Home Office and Chef's Kitchen in Longmeadow

Spacious 3BR/1.5BA home with one king & two queen beds, with three Roku TVs & AC. Chef's kitchen is fully stocked and features SubZero fridge, and new appliances. Expansive office with dual monitors & printer, perfect for remote work. Relax in the living room with a 75" TV or unwind in the fully fenced-in backyard with hammock & gazebo. Basement bedroom with private half-bath. Garage and driveway parking included. Relax with the whole family at this peaceful place to stay. The home has stairs.

Guest favourite

A modern kitchen features white cabinetry and stainless steel appliances, including a large refrigerator and an oven with a microwave above. An island with bar stools provides additional seating, while natural light filters through a nearby window, illuminating the wood flooring.

Apartment in Forest Park

4.92 out of 5 average rating, 109 reviews

Modern 3BR Near Six Flags, MGM Casino & Museums

Welcome to our renovated 3 BR bedroom apartment, thoughtfully designed for a cozy and modern stay. Ideal for families and friends, home-away-from-home atmosphere with spacious bedrooms and a fully equipped kitchen for your convenience. The apartment is located on the second floor and offers added privacy. Enjoy easy access and a prime location close to downtown, casinos, museums, Six Flags, The Big E, and local hospitals. For your convenience, two parking spaces are provided in the driveway.

Top Guest favourite

The exterior of a Cape-style home is shown, featuring light green siding and a sloped gray roof. A paved driveway leads to a two-car garage. Lush greenery surrounds the house, with flower pots positioned near the entrance and a well-maintained front lawn.

Home in Longmeadow

4.99 out of 5 average rating, 88 reviews

4 BR Entire House w/Hot Tub

This home is nestled in a family neighborhood, on a quiet road that ends with a cul-de-sac. This is a whole house rental, not a shared space. Situated about one mile from the Connecticut line, there is quick access to Rte. 91. Bradley International Airport is a 15 minute ride in light traffic. The Basketball Hall of Fame, MGM Casino, Dr. Seuss Museum, Six Flags, The Big E, Springfield Symphony Orchestra, just a few of the area attractions. Great restaurants and grocery shopping nearby.

Top Guest favourite

A cozy bedroom features a queen-size bed, dressed in soft white linens and a teal accent throw. A piece of wall art adds character above the bed. Natural light filters in through a window, complemented by light curtains. A wooden dresser provides storage space.

Home in Enfield

4.97 out of 5 average rating, 31 reviews

Nest&Rest Escape

Nest&Rest Escape is a perfect blend of comfort and convenience. Located 15 minutes from Bradley Airport and MGM Springfield Casino, and a quick 15-minute drive to Six Flags, 20 minutes to the Holyoke mall, 5 minutes drive to shopping and restaurants. 15-minute drive to Baystate Hospital. Rest& Nest Escape is ideally situated for both adventure rest and relaxation. Whether you're a professional seeking a quiet space or an adventurer looking for nearby activities. We got you!

Guest favourite

A cozy bedroom showcases a plush bed topped with decorative pillows featuring a floral pattern. A wooden accent wall adds warmth, while a low dresser and round mirror complement the space. A wall clock and small decor items enhance the room's functionality and style.

Guesthouse in Agawam

4.84 out of 5 average rating, 32 reviews

Studio ADU Guesthouse near Six Flags

Get ready for thrills and adventure! 🏞️🏰 Our cozy retreat is the perfect base for your Six Flags getaway! 🚗 Located just minutes away from the park, our home offers: Comfortable bedroom with plush bed Fully equipped kitchen for meal prep Relaxing living area for downtime Parking for your convenience Unwind after a day of roller coasters and excitement, and get ready to do it all again the next day! 😎 Book your stay with us and make your adventure unforgettable! 🏠👍

Top Guest favourite

A serene riverside deck features two striped lounge chairs, positioned for optimal views of the Connecticut River. Lush greenery frames the scene, and flower pots add a touch of elegance. The wooden deck offers a natural and inviting space to relax by the water.

Home in Agawam

4.97 out of 5 average rating, 222 reviews

Sunrise on the Water's Edge - Riverside Bungalow

Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Guest favourite

A serene riverside deck overlooks the calm waters of the Connecticut River. The space features wooden railings and is surrounded by lush greenery, with a few bare trees reflecting the change of seasons. The peaceful landscape offers a quiet spot for relaxation.

Cottage in Enfield

4.84 out of 5 average rating, 186 reviews

Hilda’s Riverside Retreat

Amazing Newly renovated Airbnb! Nestled along the meandering, Connecticut River, beautiful veiw! “Just what the doctor ordered”. And just a stone’s throw away from Downtown Springfield, MGM and Hartford. Whether you are visiting the Knowledge Corridor to visit any of the 30+ universities and liberal arts colleges, business or pleasure, This waterfront property is cozy and offers every amenity you left at home!

Guest favourite

A charming brick exterior of the retreat features multiple large windows and a welcoming front entrance. Lush green grass surrounds the property, with decorative landscaping elements visible, including flowering plants. Solar panels are situated on the roof, reflecting an eco-friendly design.

Guesthouse in Enfield

4.95 out of 5 average rating, 75 reviews

Close AirPort|SixFlags|Big E|Free Private Parking

Escape to Pineside Retreat in Enfield, CT—a tranquil haven blending comfort and nature. Conveniently located 20 minutes from Bradley Airport and MGM Springfield Casino, 15 minutes from Six Flags, 22 minutes from Holyoke Mall, 5 minutes from Scantic River State Park, and 10 minutes from Windsor Locks Canal State Park. Perfect for professionals or adventurers seeking relaxation in a cozy, rustic-modern retreat.

Top Guest favourite

A bright living area features a dark sofa with multiple cushions, flanked by two patterned chairs. A wooden coffee table is positioned in the center, and a laptop is placed on it. Natural light enters through the two windows, adorned with dark curtains.

Apartment in Enfield

4.99 out of 5 average rating, 296 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.