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.

Guest favourite
Guest suite in Winchester
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
Jan. 27 – Feb. 3
$144 CAD per night
5.0 out of 5 average rating, 95 reviews
Guest favourite
Guest suite in Burlington
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).
Aug. 27 – Sep. 3
$150 CAD per night
4.97 out of 5 average rating, 198 reviews
Guest favourite
Guest suite in Arlington
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.
Aug. 27 – Sep. 3
$266 CAD per night
4.92 out of 5 average rating, 152 reviews

Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Whole Foods Market149 locals recommend
Black Horse Tavern5 locals recommend
Lucia Ristorante / Winchester3 locals recommend
China Sky4 locals recommend
Wright-Locke Farm3 locals recommend
D'Agostino's Delicatessen5 locals recommend

Other great vacation rentals in Winchester

Guest favourite
Apartment in Woburn
Charming 1 BR private entrance apt commuters dream
Feb. 15 – 22
$196 CAD per night
5.0 out of 5 average rating, 89 reviews
Guest favourite
Cottage in Winchester
The Little House - A Historic New England cottage
Dec. 31 – Jan. 7
$498 CAD per night
4.96 out of 5 average rating, 47 reviews
Guest favourite
Apartment in Woburn
Comfy-Spacious-private 1BR conveniently located
Dec. 27 – Jan. 3
$210 CAD per night
4.98 out of 5 average rating, 99 reviews
Guest favourite
Home in Winchester
3 Bedroom Boston-area Gem
May 30 – Jun. 6
$454 CAD per night
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Stoneham
Explore Stoneham
Jan. 14 – 21
$153 CAD per night
4.96 out of 5 average rating, 47 reviews
Guest favourite
Home in Woburn
Spotless/Spacious home, 20 min to Boston
Sep. 1 – 8
$472 CAD per night
4.92 out of 5 average rating, 37 reviews
Guest favourite
Home in Woburn
Stone Cottage with meadow view
Aug. 16 – 23
$591 CAD per night
4.96 out of 5 average rating, 28 reviews
Guest favourite
Apartment in Woburn
Your Cozy 1 BR Apt & Relaxing Retreat
Sep. 15 – 22
$481 CAD per night
4.93 out of 5 average rating, 54 reviews
Guest favourite
Guest suite in Arlington
★Modern Studio-Private Entrance,Washer+Dryer★
Jan. 17 – 24
$204 CAD per night
4.9 out of 5 average rating, 68 reviews
Guest favourite
Home in Woburn
Large 4Bed 2Bath Clean Alternative to Hotel Living
Sep. 3 – 10
$585 CAD per night
4.86 out of 5 average rating, 99 reviews
Guest favourite
Apartment in Burlington
The Robins Nest
Jun. 15 – 22
$274 CAD per night
4.99 out of 5 average rating, 94 reviews
Guest favourite
Guest suite in Arlington
Spacious 1-BR apt+parking+laundry. 2nd BR option
Jul. 5 – 12
$215 CAD per night
4.92 out of 5 average rating, 36 reviews

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

$41 CAD before taxes and fees

Destinations to explore