Vacation rentals in Winchester
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
Apartment in Waltham
4.98 out of 5 average rating, 209 reviewsCozy 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)
Sep 23 – 30
Apartment in Woburn
4.97 out of 5 average rating, 102 reviewsComfy-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!
Nov 7 – 14
Guest suite in Burlington
4.97 out of 5 average rating, 199 reviewsRelaxing 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).
Feb 11 – 18
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Guest suite in Melrose
4.93 out of 5 average rating, 487 reviewsPrivate & Cozy Suite -near Bost-Airp-Salem-Train
Jul 5 – 12
Guest suite in Winchester
5.0 out of 5 average rating, 97 reviewsWarm and cozy 1st flr sweet guest suite w parking
Jan 13 – 20
Apartment in Woburn
5.0 out of 5 average rating, 91 reviewsCharming 1 BR private entrance apt commuters dream
Nov 10 – 17
Cottage in Winchester
4.96 out of 5 average rating, 47 reviewsThe Little House - A Historic New England cottage
Oct 20 – 27
Home in Winchester
5.0 out of 5 average rating, 5 reviews3 Bedroom Boston-area Gem
Sep 13 – 20
Guest suite in Arlington
4.92 out of 5 average rating, 36 reviewsSpacious 1-BR apt+parking+laundry. 2nd BR option
Jul 29 – Aug 5
Guest suite in Arlington
4.92 out of 5 average rating, 90 reviewsStylish Studio - ✓Sanitized ✓Private ✓Spotless
Mar 7 – 14
Guest suite in Arlington
4.95 out of 5 average rating, 42 reviewsCharming 1Bd Apt. in Historic Arlington Home
Feb 20 – 27
Home in Woburn
4.97 out of 5 average rating, 29 reviewsStone Cottage with meadow view
Sep 26 – Oct 3
Home in Stoneham
4.96 out of 5 average rating, 47 reviewsExplore Stoneham
Jan 24 – 31
Apartment in Stoneham
4.99 out of 5 average rating, 90 reviewsCozy Basement Apartment-Stoneham
Aug 31 – Sep 7
Home in Woburn
4.92 out of 5 average rating, 37 reviewsSpotless/Spacious home, 20 min to Boston
Apr 16 – 23
Quick stats about vacation rentals in Winchester
Total rentals | 20 properties |
---|---|
Wifi availability | 20 properties include access to wifi |
Rentals with dedicated workspaces | 10 properties have a dedicated workspace |
Family-friendly rentals | 10 properties are a good fit for families |
Total number of reviews | 900 reviews |
Nightly prices starting at | $30 before taxes and fees |
Frequently Asked Questions
Are there family-friendly vacation rentals in Winchester?
Winchester has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Where should I stay in Winchester?
Make yourself at home in Winchester by choosing from our most frequently booked neighborhoods. We have over 130 vacation rentals in Winchester Highlands, over 130 vacation rentals in Shakerhill, and over 1,960 vacation rentals in Wedgemere.
Are there vacation rentals with a dedicated workspace in Winchester?
Yes! Work meets play with ease at over 10 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Winchester have wifi?
Absolutely! We offer over 10 house rentals with wifi in Winchester. Enjoy a tailored experience with all the comforts you desire.
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