Holiday rentals in Longmeadow

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Top-rated holiday rentals in Longmeadow

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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
4.94 out of 5 average rating, 17 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.

Top guest favourite
A light-filled living area features a cozy sofa and elegant chairs arranged around a delicate coffee table. A decorative fireplace serves as a focal point, complemented by soft curtains and a tasteful chandelier. An ornate mirror reflects the natural light streaming through the large windows.
Guest suite in Enfield
5 out of 5 average rating, 161 reviews

Luxe 1822 Apt | Rain Shower | Plush beds | Firepit

Oversized 1800sf apartment is a 2-story unit, front half of a 200-year-old former schoolhouse in Enfield's historic district. The antique colonial is set up as a side-by-side duplex with private apartment occupying the front 1/2 of house & the owner's unit in the back with a separate driveway entrance & door. EXTRAS: ❋ PRIVATE USE OF POOL & PATIO ❋ KEYCODE CHECK-IN ANYTIME ❋ COFFEE/TEA BAR WITH EVERYTHING NEEDED ❋ POPCORN MACHINE, SNACKS & DRINKS ❋ 4 TVs: YOUTUBE TV, MAX, NETFLIX, WIFI

Guest favourite
A cozy living area features a green sofa adorned with colorful floral cushions. A coffee table with a light-colored surface is centered on warm wooden flooring. In the background, a dining area with dark chairs is visible, alongside an archway leading to the kitchen.
Home in Longmeadow
4.96 out of 5 average rating, 85 reviews

★Unique Suburban Retreat Cozy Comfy Pet Friendly★

WOW This comfortable three bedroom home is located in an excellent neighborhood. Recently renovated with all new kitchen appliances, its fresh, clean and spacious. Free, ✔high speed WiFi ✔cable TV ✔coffee ✔washer/dryer ✔garage ✔fenced in yard ✔pet friendly ✔central air ✔heat ✔smart TVs in every bedroom ✔ Linens, towels, toiletries provided Perfect Location, just a short drive to all the area attractions ✔MGM ✔Mass Mutual Center ✔Basketball Hall Of Fame ✔6 Flags ✔The Big E ✔Dr Seuss Museum,

Top guest favourite
A spacious living area is furnished with a gray sectional sofa, accented with colorful throw pillows. A wooden coffee table is placed in front, on a soft area rug. Two large windows allow natural light to brighten the room, complemented by ceiling fans and tasteful decor.
Loft in Tolland
4.96 out of 5 average rating, 303 reviews

Cozy studio loft

Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

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, 29 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.
Guest house in Agawam
4.81 out of 5 average rating, 27 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 comfortable studio space is highlighted by a plush queen bed adorned with white bedding, positioned beside a cozy fireplace. Soft light is provided by a bedside lamp, while a fan offers air circulation. Neutral tones and warm accents create a welcoming ambiance.
Flat in Wilbraham
4.99 out of 5 average rating, 135 reviews

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Top guest favourite
The entrance of the historic home is framed by carefully manicured hedges and trees. A path leads to an elegant front door, flanked by large windows. Decorative wall lanterns add charm to the exterior, capturing the welcoming essence of the property.
Villa in Longmeadow
5 out of 5 average rating, 59 reviews

Comfort and Luxury - 180 year Old Gothic Estate

This 180 year old home provides luxury and comfort for up to 10 guests. Perfect for family gatherings or a group of friends wanting to get away . Chef prepared meals and house keeping services are offered at additional rates. Conveniently located only 15 miles north of Hartford/Springfield BDL Airport and a 5 minute drive to Springfield's MGM casino. PLEASE note that guest of record is required to have at least 3 Five Star reviews in order to book

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
4.98 out of 5 average rating, 216 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 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.
Guest house in Enfield
4.94 out of 5 average rating, 70 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
The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.
Guest house in Granby
4.98 out of 5 average rating, 875 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

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 quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

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.
Flat in Enfield
4.99 out of 5 average rating, 289 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.

Popular amenities for Longmeadow holiday rentals