Holiday rentals in Woburn

Guest suite in Winchester

5 out of 5 average rating, 214 reviews

Warm and cozy 1st flr sweet guest suite w parking

Easy living at this peaceful and centrally-located guest suite. Winchester is the quintessential New England town located just 8 miles from Boston with an easy drive or 16 minute by train from Winchester Center or Wedgemere. Or check out historic Lexington and Concord next door, bustling Arlington Center or hip Davis Square. Tufts University, Harvard Square, Harvard University and MIT nearby. Your comfortable home away from home for fun excursions, get aways, business meeting or college visits

5 out of 5 average rating, 15 reviews

Flat in Winchester

Winchester Apartment on Greenway

Updated apartment with hardwood floors, full kitchen and washer/dryer, next to Davidson Park, Tri-Community Greenway and the Community sport complex. A wonderful short walk down the Greenway takes you to Leonard Pond for tennis, pickleball, soccer or frisbee. A 20-minute walk down the Greenway takes you to Winchester Center for restaurants, shops and train to Boston. Or walk four blocks east to explore the 2,000-acre Middlesex Fells Reservation. Route 93 access is less than a 5-minute drive.

4.95 out of 5 average rating, 189 reviews

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

5 out of 5 average rating, 154 reviews

Charming 1 BR private entrance apt commuters dream

Newly renovated, spacious 1 B/R apartment. Featuring a private entrance, kitchen with all new stainless-steel appliances, eating/office area, living room and separate bedroom with a Queen-sized bed, streaming cable & WIFI connections, exclusive outdoor space and off-street-parking. Minutes to Rt 95, Rt 128, Rt 93. Easy drive to all major local business, hospitals, mass transportation , airport & commuter rail less than 2 miles. Minutes to Woburn center, Winchester center, shopping & dining.

4.83 out of 5 average rating, 35 reviews

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

5 out of 5 average rating, 36 reviews

Home in Woburn

Large House- 16 mins to Boston + on site parking

Make yourself at home in this 4-bedroom Woburn retreat. With 3 queen bed, 1 full beds, and 2 twin bed, there's plenty of space for everyone to get a good night's sleep. The adorable living room features a cozy sofa bed, perfect for lounging and watching movies. The open kitchen leads to the dining room for family dinners. Enjoy the convenience of amenities like a hair dryer, washing machine, AC, WiFi, and heating. The bathrooms are equipped with showers for a refreshing start to your day.

4.92 out of 5 average rating, 187 reviews

Flat in Arlington

Dixie’s House, 1BD in Arlington

1 bedroom, family-friendly apartment in the quiet Morningside neighborhood of Arlington. Can sleep 5. Free driveway & off-street parking. King bed + queen sofa bed in living room, 1 full bath, coffee, microwave, toaster oven, foreman grill, rice maker & dishwasher. 1 mile from the bike path and short drive to Alewife MBTA and Davis Square. Young kids and dog live above (expect some noise). Bus route leads to Harvard Square nearby. Also close to Wright-Locke Farm with stunning fall hikes.

4.98 out of 5 average rating, 164 reviews

Guest suite in Woburn

Relaxing and Comfortable Home Away From Home

Privacy and comfort in complete lower level of this home. Private entrance and no shared space all within 5 minutes of shopping/restaurants and major highways. The space features a large kitchen w/dining area for 4pp, 1 bedroom with queen sized bed , living room with 65 inch tv with full cable. 1 full Bathroom with shower and tub. Washer and dryer are also included. Professionally maintained and enclosed backyard and patio area for outdoor seating.Full sized bed in the bonus room.

4.93 out of 5 average rating, 161 reviews

Your Cozy 1 BR Apt & Relaxing Retreat

Welcome to your romantic 1-bedroom apartment in Woburn, the ultimate escape for couples looking for relaxation and charm. Enjoy a private jacuzzi 🛁 and a cozy fire pit 🔥—ideal for creating unforgettable memories. Step right out from the bedroom to the jacuzzi and outdoor space, allowing you to unwind in the soothing waters while enjoying the warm ambiance of the fire pit. Perfect for a romantic retreat, this intimate space provides everything you need for a truly enchanting stay.

4.89 out of 5 average rating, 214 reviews

Guest suite in Medford

Beautiful 1 Bedroom, 1 Bathroom in Medford

Come stay in this recently renovated, very comfortable space situated in a quiet neighborhood across the street from the Brooks Estate woods, just outside of Boston. The house itself is a historical gothic cottage built in 1856 and is the 2nd oldest home in the area. The space is in a historic single family home and both the bedroom and bathroom are 100% PRIVATE and separated from the rest of the house with a private entrance. It's on the first floor so there are no stairs!

4.86 out of 5 average rating, 199 reviews

Guest suite in Reading

Spacious Suite-Private Entrance-Near Boston/Salem

Spacious suite in quiet neighborhood with private entrance & access to entire ground level - private bath, living room, & bedroom - queen bed, 2 twin beds, couch & air bed if needed for children. Outdoor patio, washer/dryer, A/C (seasonal), coffee, microwave, fridge, Wi-Fi Keypad on door - come & go as you please. 3 minutes to I-95, I-93, & 20 min. to Boston. Train to downtown 1 mile away. 13 miles to Salem (abt 20 minutes w/o traffic). Accommodates up to 6 (4 adults max)