Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

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Guest favourite

Guest suite in Winchester

5.0 out of 5 average rating, 106 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

1 – 8 Jan

$1,400 AUD total

Guest favourite

Apartment in Waltham

4.98 out of 5 average rating, 210 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)

12 – 19 Dec

$1,556 AUD total

Guest favourite

Apartment in Woburn

4.95 out of 5 average rating, 110 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!

31 Jan – 7 Feb

$1,644 AUD total

Guest favourite

Guest suite in Burlington

4.98 out of 5 average rating, 209 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).

31 Jan – 7 Feb

$1,169 AUD total

Guest favourite

Guest suite in Arlington

4.92 out of 5 average rating, 158 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

$2,001 AUD total

Guest favourite

Apartment in Lexington

4.94 out of 5 average rating, 338 reviews

Warm home in Lexington, walk to town, nature trail

A newly built in-law apartment, located in the historical Lexington, is welcoming travelers home. Located in a safe and friendly community, the apartment is convenient to town center, Boston, restaurants, shops, tourist spots, and Lower Vine Brook forest trail (1 min walk)! The apartment follows enhanced cleaning protocol, with thorough ventilation and disinfecting. The HVAC system is private. Checkin and checkout are easy and no-contact. Registered with the town of Lexington: STML-21-2.

24 – 31 July

$2,829 AUD total

Guest favourite

Apartment in Cambridge

4.94 out of 5 average rating, 466 reviews

Spacious Strawberry Hill Suite (West Cambridge)

This 3rd floor suite is less than 2 miles west of Harvard Sq. You'll have exclusive access to the space, which has a full bathroom and kitchenette. There is a queen bed suitable for two people and the couch in the living room converts to a bed for one. Our neighborhood is friendly, safe, and has a lot to offer. Public transportation (bus) is a 5 minute walk. The trip to Harvard Square is 10-15 minutes. I live in the home downstairs and am available should you need me during your stay.

8 – 15 June

$1,659 AUD total

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.

28 Oct – 4 Nov

$1,727 AUD total

Guest favourite

Apartment 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.

28 Dec – 4 Jan

$1,920 AUD total

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.

2 – 9 Nov

$1,728 AUD total

Guest favourite

Apartment in Arlington

4.98 out of 5 average rating, 175 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

23 – 30 Jan

$2,019 AUD total

Guest favourite

Home in Medford

4.95 out of 5 average rating, 126 reviews

Single family home near Tufts,DT Boston,w/ parking

Gather at this attractive contemporary 1,894 sq ft single family cape for a relaxed homemade dinner for family or friends in the oversized kitchen. Spread out on the couch in the living room that has a cabin feel to it, or head out to Fenway Park or the bar from Cheers, but dig a little deeper below the surface and you'll find a surprising wealth of things that make Boston one of the best cities in America, and the world. Please make sure you read all the details before booking.

22 – 29 Sept

$9,636 AUD total