Vacation rentals in Ludlow

Lemnos Experience/Game RM/MGM/BigE/SIX FLAGS

A peaceful, cozy, family-friendly retreat prioritizing safety and comfort. Our stylish space offers a luxurious yet welcoming atmosphere, ideal for relaxing and creating memories with loved ones. Conveniently located at sixteen Acres near Springfield Basketball Hall of Fame, Western New England, MGM Casino, Big E, Forest Park, Massachusetts Mutual, Six Flags, Bradley Airport, and just 45 minutes from the Berkshires and 30 minutes to UMass Amherst. Perfect for friends and families experiences!

Family · Location · Hospitality

Serene 1-br suite on 75 acre horse property

Escape to a peaceful 1-bedroom suite on a beautiful 75-acre horse property. Tucked into the woods 1/3 mile from the main road, enjoy privacy, scenic nature trails, and views of up to 20 horses grazing in the pastures outside your windows. Relax in the guest gazebo with front-row views of the horses, perfect for morning coffee or unwinding outdoors. Enjoy a private entrance, dedicated workspace, and high-speed WiFi. Conveniently near Amherst, UMass, Smith, and Mount Holyoke Colleges.

Family · Value · Kitchen

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

Location · Indoor spaces · Check-in

Tiny House Farm Retreat: Mountain Views, Fire pit

The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Family · Value · Comfort

Craig's Cove

Craig's Cove is a two-room apartment (in my finished basement) with a farmhouse industrial motif and is in close proximity to Sturbridge, wineries, micro-brews such as Lost Towns Brewing, and beautiful scenery. Guests will be provided with one off-street parking space, private entry, bedroom with queen-size bed, full bathroom, TV with Netflix & Amazon Prime, free wifi, coffee, kitchenette with sink, microwave, fridge, toaster oven, hot plate (no full size stove), and patio with pergola.

Family · Location · Air conditioning

King Bed w/ Game Room near Massmutual w/ Riverview

Enjoy a stylish, spacious stay in this fully renovated home with nicely decorated bedrooms, two full baths, a full kitchen plus kitchenette, and dining for eight. Have fun in the game room with pool, arcade games, soccer board game, archery, and a huge TV. Relax on the large patio with a beautiful Connecticut River view. Perfect for families and groups seeking comfort, entertainment, and convenience. It’s also near Memorial Dr. and many local attractions and dining.

Value · Family · Hospitality

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.

Location · Family · Indoor spaces

Clean/Spacious 1 bedroom house! (w/parking & yard)

You have the entire space to yourself. Newly painted. Newly refinished hardwood floors throughout. Dining room, Living Room and Kitchen and Front porch, back porch and fenced-in Backyard all for your use. ~Pet fee is $100 for up to 1 pet, $40 for additional pet[per night, they are added guests]~{please add them in your guest count, as I prepare for their stay, as well!} ~ MAXIMUM PETS ALLOWED IS 2 ~ LEVEL 2 EV charger & Tesla adapter AVAIL upon request

Family · Value · TV

The View Guest Suite - Amherst

Looking for the perfect place to stay in the five colleges area? The View Guest Suite - Amherst is now open and ready for you. Two luxurious King bedrooms and shower baths, full kitchen, dining area and living room for three non-smoking guests just minutes away from all of the action. Full lower floor in a newly built eco-friendly property, picture windows, spectacular views of the Pioneer Valley, your own decks, entrance and self check-in.

Family · Location · Bathroom

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.

Location · Family · Sleep quality

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!

Family · Location · Quiet

Newly Built Barn Loft in Pioneer Valley

Newly Built Barn Loft: Walk to Belchertown Common & McCarthy's Pub. Conveniently located near all Five Colleges—12-minutes to Amherst and UMass, and 20-minutes to Springfield's Casino and Basketball Hall of Fame. Enjoy nearby bike paths, hiking trails, the Quabbin Reservoir, and other local Pioneer Valley attractions. Perfect for experiencing Western Mass!

Value · Family · Condition