Holiday rentals in Longmeadow

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Top-rated holiday rentals in Longmeadow

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Top guest favourite

Guest suite in Agawam

4.96 out of 5 average rating, 186 reviews

The Waters Edge

Entire 1st floor, private Guest Suite in a contemporary home located on the scenic Ct River. Centrally located btwn Bstn & Htfd. 1 mile to Six Flags, 10-15 min to Suffield Academy, The Big E, Eastern States Exposition, Bradley Intnl Airport, MGM, bsktbl & volybl Hall of Fame, 30-40 min The Bushnell, 5 College Campus area. The CT River is home to beautiful wildlife. Protected lands provide a stunning backdrop to picturesque views. Rest's, museums, hiking, shopping & more. NO SMOKING PROPERTY.

Top guest favourite

Guest suite in Enfield

5 out of 5 average rating, 135 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

Top guest favourite

Cottage in Southwick

4.98 out of 5 average rating, 109 reviews

4 Kayaks Fire Pit & Lake Views from Hot Tub

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Guest favourite

Home in Longmeadow

4.96 out of 5 average rating, 81 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

Home in Longmeadow

4.98 out of 5 average rating, 56 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.

Superhost

Home in Enfield

5 out of 5 average rating, 3 reviews

Nest&Rest Escape

Rest&Nest Escape is a perfect blend of comfort and convenience. Just 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!

Top guest favourite

Flat in Wilbraham

4.98 out of 5 average rating, 111 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.

Superhost

Home in Agawam

4.82 out of 5 average rating, 28 reviews

Home near Six Flags/ hot tub

Escape to our picturesque haven, perfectly situated just minutes from Six Flags thrill rides! This spacious, 11-person retreat combines rustic elegance with modern comforts, ensuring an unforgettable getaway. Unwind under starry skies in our bubbling hot tub, backyard includes patio furniture. This apartment sleeps comfortably up to 11 guests- 3 bedroom. 1st Bedroom - 2 queen beds (master suit) 2nd Bedroom - twin, queen 3rd Bedroom - bunk: twin over full, twin

Top guest favourite

Villa in Longmeadow

5 out of 5 average rating, 54 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

Guest favourite

Home in Enfield

4.95 out of 5 average rating, 61 reviews

Cozy First Floor Living Nestled in the Woods

Visiting family in the area? Traveling to Springfield or Enfield for sports? This home away from home will make you feel like you never left! The warm and welcoming decor will make you feel right at home and allow you to unwind from your travels. Enjoy a fully equipped kitchen at your leisure, with an array of seasonings available for use. Let the stress go with what to pack because this home offers everything you need for your stay.

Top guest favourite

Home in Agawam

4.98 out of 5 average rating, 174 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

Guest house in Enfield

4.83 out of 5 average rating, 36 reviews

Close BDL AirPort & SixFlags 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.