Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

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Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Whole Foods Market149 locals recommend
Horn Pond10 locals recommend
Lord Hobo Brewing Company7 locals recommend
D'Agostino's Delicatessen5 locals recommend
Black Horse Tavern5 locals recommend
The Brickyard4 locals recommend

Other great vacation rentals in Winchester

Top guest favorite
A serene beach scene features soft, sandy shores framed by scattered patches of grass. Gentle waves can be seen lapping at the shoreline, under a sky adorned with fluffy clouds and scattered blue areas, creating a tranquil coastal atmosphere.
Home in Ipswich
5 out of 5 average rating, 22 reviews

Capeview Cottage

GillianRating, 5 stars5 months ago
This place had the most amazing view.
Guest favorite
Home in Ipswich
4.88 out of 5 average rating, 101 reviews

Hillside Ocean View 2BR with Private Beach Access

TaniaRating, 5 stars2 weeks ago
We love Ipswich and are so glad to find this gem of Airbnb. Mark's communications are topnotched and he proactively checked in with us to ensure that everything is alright. The house has everything we needed and more....not just for short stays but equally suitable for longer stays too. The bed and pillows were very comfortable. The house heating system is very efficient and heats up the whole house quickly and comfortably for the few cold days we were staying there. My husband loved having a dedicated work space which had a beautiful water view. There were plenty of supplies in the kitchen, bathroom and laundry. Everything is very well thought out. It might be an older house but it's very quaint, cosy and quintessentially New England. Although we had several days of lousy weather.... we still managed to do plenty out of the few half days when the skies cleared out. Oh and thank you for the very lovely cranberry banana bread... its one of the best that we've ever eaten.
Top guest favorite
A fire pit is surrounded by colorful adirondack chairs in a grassy area, with bright yellow flowers adding a pop of color. The view in the background includes a landscape of greenery leading to the water, suggesting a peaceful outdoor space for gatherings.
Home in Ipswich
4.98 out of 5 average rating, 194 reviews

Stagehill Beach House

PaulaRating, 5 stars6 months ago
Loved this rental! Katie was so nice and very accommodating! This house was great! Pictures didn’t do it justice! Plenty of room and amazing views. My favorite room was the sitting room upstairs with views from every window! Lots of clean linens and super comfy beds! Check in and check out were a breeze. Easy to follow instructions on how to close up. Only complaint was on me! Wish we booked “in season” to take advantage of the beach! We will definitely be back! Thank you again, Katie! Your place and you, were top notch!
Top guest favorite
The kitchen features modern white cabinetry and a marble countertop. A stainless steel gas range and exhaust hood are prominently displayed. Natural light from a window illuminates a nearby sink, which is accompanied by a potted orchid and overlooks a serene view of the meadow.
Apartment in Brighton
4.99 out of 5 average rating, 80 reviews

New 3 bedroom, 2 bath unit, meadow view!

CiaraRating, 5 stars2 days ago
Simon elevates hosting to a whole new level and provides a tough act to follow. He pays attention to detail and has carefully considered and included all the things that will make you feel both welcomed and comfortable. The home is spotless, very modern and tastefully decorated. The linens are of a great quality and the beds are super comfortable. The master shower is wonderful, and Simon has so thoughtfully provided amenities in the bathrooms and the kitchen. The location of the home is great in a quiet neighborhood with parking spaces provided. The home has lovely natural light and even great views out of the windows. Both Simon and his home is a standout and so far, my best experience with Airbnb to date. Simon goes above and beyond to make your stay a luxurious one and by that, he makes it hard to leave but easy to want to return to.
Guest favorite
A serene park scene is shown, with a sandy area leading to a calm body of water. People can be seen enjoying various activities under a partly cloudy sky, framed by lush greenery and large trees. A sign for Arlington Recreation is prominently displayed.
Guest suite in Arlington
4.85 out of 5 average rating, 82 reviews

★Modern Studio-Private Entrance,Washer+Dryer★

BrianRating, 5 stars4 months ago
Had a great stay at this place (this was our second time there). Our plane to the area was much delayed but our hosts were understanding and very helpful. Everything was as advertised and the place was convenient to our activities visiting family. Will definitely stay there again!
Top guest favorite
A full moon casts a golden glow over the water, illuminating the surface with shimmering reflections. In the background, two large houses with red roofs are visible, set against a twilight sky.
Apartment in Swampscott
4.98 out of 5 average rating, 40 reviews

Ocean View Apartment 2nd Floor

SherylRating, 5 stars6 months ago
We have had a lot of luck with AirBnB, but Valeri's place was the best so far. Literally across the street from beach access. A great restaurant next door with several others in easy walking distance. Minutes from Salem and Marblehead. The rental was fantastic. You could and picture it as being what you would want in a seaside vacation getaway or second home. Everything was clean, stocked, and organized. Beds were comfortable, and it was just a really all around relaxing environment. Loved the decor! Valeri was very nice and gave great local recommendations. I don't check to see if she's a "super" host, but she's number one for me. Loved our weekend getaway and would absolutely book again.
Superhost
A well-lit staircase leads to a glass door, framed by planters that hold various greenery. Soft lighting casts gentle shadows along the steps, creating a serene and inviting entrance.
Apartment in Whitinsville
5 out of 5 average rating, 3 reviews

Attractive Lower Level Guest Suite

PatrickRating, 5 stars1 month ago
This was a great place for us to stay. The place was clean and it was a great location for our plans. The host was friendly and made the stay enjoyable. I will be staying here on my next visit to the area.
Superhost
Apartment in Cambridge
4.8 out of 5 average rating, 20 reviews

Elegant 3-Bed Oasis in Cambridge Near Harvard/MIT

JesseRating, 5 stars4 months ago
Beautiful property and excellent location. Extremely convenient for our family to enjoy thanksgiving with family. Excellent communicators and very flexible with our travel schedule.

Quick stats about vacation rentals in Winchester

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

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 2,150 vacation rentals in Wedgemere, over 120 vacation rentals in Shakerhill, and over 120 vacation rentals in Winchester Highlands.

  • Are there vacation rentals with a dedicated workspace in Winchester?

    Yes! Work meets play with ease at over 20 vacation rentals in Winchester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in Winchester?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

  • Do house rentals in Winchester have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Winchester. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winchester have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Winchester. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Winchester?

    Experience the best of Winchester with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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