Holiday rentals in Winchester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 104 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

9–16 Sep

$171 SGD per night

Guest favourite

Flat in Waltham

4.98 out of 5 average rating, 209 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You will love this large 400 sq. ft private 1 bedroom studio. This unit has a private entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

7–14 Feb

$170 SGD per night

Guest favourite

Flat in Concord

4.95 out of 5 average rating, 164 reviews

Mema's Place --Lovely apartment in private home

This private apartment in a lovely home in historic Concord, Massachusetts features one bedroom with queen bed, living room, kitchen, bathroom, and porch. Your apartment is locked off from the rest of the home and you have your own entrance. We are within 4 miles of Concord Academy, Middlesex School, the North Bridge, Sleepy Hollow Cemetery (where Alcott, Thoreau, Emerson, and Hawthorne are buried). Discounts for stays of longer than 2 weeks.$75 additional cleaning fee for stays over 2 weeks.

22–29 Jan

$197 SGD per night

Guest favourite

Flat in Woburn

4.94 out of 5 average rating, 107 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!

13–20 Nov

$183 SGD per night

Guest favourite

Guest suite in Burlington

4.98 out of 5 average rating, 202 reviews

Relaxing 2 Room Suite with Private Bath/Deck/Patio

Welcome to this spacious, quiet and relaxing furnished suite (private entrance own deck- patio-fire pit). It is truly in an amazing location; walking distance to Mall/Lahey Hospital & only 18 mi from Boston Logan Airport, with plenty of parking. Our place is good for professionals, students, couples, solo, families (with kids). The airbnb is attached to a main house but it's contactless (check-in/-out) with own entrance. Ideal for 2, a little tight for 3 but manageable (sofa into bed).

20–27 Apr

$132 SGD per night

Guest favourite

Guest suite in Arlington

4.92 out of 5 average rating, 156 reviews

Cozy 1 bed apt Cambridge/Somerville/Arlington line

Our location is only 1.2 miles from Tuffs University and 2.4 from Harvard University. It is in the middle of North Cambridge, Somerville, and Medford. You could walk to Davis Square or to downtown Arlington and will find plenty of good restaurants and coffee places to explore. It is only 3 minutes to public transportation, bus that connects with Red line in the MBTA subway system. Our residential neighborhood is young and vibrant, and excellent point to explore Boston and surrounding towns.

16–23 Nov

$218 SGD per night

Guest favourite

Guest suite in Watertown

4.91 out of 5 average rating, 264 reviews

Private 1BR Pied-a-terre

Fully furnished mini-suite with private entrance; walk in at ground level. Picture window view of, and use of, large back yard. Separate sitting and sleeping areas (full size bed), desk/workspace, bathroom with shower, kitchenette with small fridge, coffeemaker and microwave (no stove). Great take-out nearby. No pets, no smoking permitted. Car? There is off-street covered parkling. No car? 71 Bus to Harvard Square stops at our corner; short walk to other buses and public transportation.

18–25 Nov

$130 SGD per night

Guest favourite

Guest suite in Peabody

4.98 out of 5 average rating, 177 reviews

Cozy West Peabody Guest Suite

Come enjoy this renovated studio guest suite in the quiet neighborhood of West Peabody! An easy drive to Salem or Boston, close to a woodsy bike trail, and a short drive to local shops and restaurants. Features a fully equipped kitchenette and an outdoor space with a fire pit and charcoal grill. Make use of a Roku TV and fast, reliable WiFi to keep yourself entertained. This is a great space whether you are looking to explore the Boston North Shore or simply embark on a quiet getaway.

9–16 Aug

$162 SGD per night

Guest favourite

Guest suite in Woburn

4.97 out of 5 average rating, 148 reviews

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.

23–30 Nov

$188 SGD per night

Guest favourite

Flat in Medford

4.92 out of 5 average rating, 258 reviews

Garden Apartment for Vacation & Business Travelers

The perfect place to rest, relax or work. Visit universities, Salem or family and friends in the area. This English Basement apartment is located on the Mystic River, 10 minutes from Harvard University in Cambridge and 20 minutes from the City of Boston. Enjoy many local outdoor amenities including the Mystic Lakes, parks, playgrounds, tennis/basketball courts and jogging paths, all behind our house. We warmly welcome people from all backgrounds as we value and respect diversity.

26 Mar – 2 Apr

$224 SGD per night

Guest favourite

Guest suite in Melrose

4.84 out of 5 average rating, 240 reviews

Guest Suite with separate entrance

Guest Suite with open floor plan (kitchen with stove/oven, refrigerator, microwave, bottled water dispenser); living area (pullout couch, loveseat, 50" TV with Roku and Netflix); sleeping area, bathroom with shower, separate entrance, 1 off-street parking space. Convenient to public transportation (commuter rail - 5 min walk, 12 min ride to Boston/45 min ride to N Shore; subway - 2 min walk to bus/subway (25-40 min ride to Boston) or drive (25-45m to Boston or 45-60m to N Shore).

10–17 Nov

$152 SGD per night

Guest favourite

Flat in Arlington

4.98 out of 5 average rating, 174 reviews

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom Private from public, patio and hot tub overlooks lake and conservation land. No stairs Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit $25.00 pet fee Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures are followed

11–18 Nov

$203 SGD per night