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 favorite

Apartment 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)

Sep 23 – 30

$108 per night
Guest favorite

Apartment in Woburn

4.97 out of 5 average rating, 102 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!

Nov 7 – 14

$125 per night
Guest favorite

Guest suite in Burlington

4.97 out of 5 average rating, 199 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).

Feb 11 – 18

$85 per night

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 favorite

Guest suite in Melrose

4.93 out of 5 average rating, 487 reviews

Private & Cozy Suite -near Bost-Airp-Salem-Train

Jul 5 – 12

$89 per night
Guest favorite

Guest suite in Winchester

5.0 out of 5 average rating, 97 reviews

Warm and cozy 1st flr sweet guest suite w parking

Jan 13 – 20

$88 per night
Guest favorite

Apartment in Woburn

5.0 out of 5 average rating, 91 reviews

Charming 1 BR private entrance apt commuters dream

Nov 10 – 17

$109 per night
Guest favorite

Cottage in Winchester

4.96 out of 5 average rating, 47 reviews

The Little House - A Historic New England cottage

Oct 20 – 27

$298 per night
Guest favorite

Home in Winchester

5.0 out of 5 average rating, 5 reviews

3 Bedroom Boston-area Gem

Sep 13 – 20

$277 per night
Guest favorite

Guest suite in Arlington

4.92 out of 5 average rating, 36 reviews

Spacious 1-BR apt+parking+laundry. 2nd BR option

Jul 29 – Aug 5

$107 per night
Superhost

Guest suite in Arlington

4.92 out of 5 average rating, 90 reviews

Stylish Studio - ✓Sanitized ✓Private ✓Spotless

Mar 7 – 14

$111 per night
Guest favorite

Guest suite in Arlington

4.95 out of 5 average rating, 42 reviews

Charming 1Bd Apt. in Historic Arlington Home

Feb 20 – 27

$114 per night
Guest favorite

Home in Woburn

4.97 out of 5 average rating, 29 reviews

Stone Cottage with meadow view

Sep 26 – Oct 3

$316 per night
Superhost

Home in Stoneham

4.96 out of 5 average rating, 47 reviews

Explore Stoneham

Jan 24 – 31

$83 per night
Guest favorite

Apartment in Stoneham

4.99 out of 5 average rating, 90 reviews

Cozy Basement Apartment-Stoneham

Aug 31 – Sep 7

$102 per night
Guest favorite

Home in Woburn

4.92 out of 5 average rating, 37 reviews

Spotless/Spacious home, 20 min to Boston

Apr 16 – 23

$258 per night

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.

Destinations to explore