Winchester holiday rentals

We found 2,508 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Winchester to find one that's perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include a garden and pool. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Winchester

Showing deals for:18 Dec - 25 Dec

Private kitchen
Interior
Dining
Exceptional
(96 reviews)

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Boston

8% off
AU$15,675
for 7 nights, 1 home
AU$2,239 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Interior
Exterior detail
Interior
Outdoor dining
Exceptional
(6 reviews)

Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17

Newton

9% off
AU$25,250
for 7 nights, 1 home
AU$3,607 per night
includes taxes & fees
Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17
Room
Living area
Private kitchen
Room
Exceptional
(14 reviews)

Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station

Boston

20% off
AU$7,372
for 7 nights, 1 home
AU$1,053 per night
includes taxes & fees
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Exterior detail
Property grounds
Interior
Sitting room
Exceptional
(21 reviews)

Charming 2-bedroom house with a hidden garden in lovely Cambridge.

Cambridge

8% off
AU$4,699
for 7 nights, 1 home
AU$671 per night
includes taxes & fees
Charming 2-bedroom house with a hidden garden in lovely Cambridge.
Interior
Interior
Bathroom
Interior
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
AU$5,885
for 7 nights, 1 home
AU$841 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Outdoor dining
Living area
Private kitchen
Room
Exceptional
(43 reviews)

Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH

Boston

8% off
AU$7,649
for 7 nights, 1 apartment
AU$1,093 per night
includes taxes & fees
Stately on Cedar - Luxe 2-bedroom Beacon Hill apartment with AC, WiFi near MGH
Interior
Living area
Room
Dining
Exceptional
(78 reviews)

The Pistachio Room at TPH - Boston

Boston

7% off
AU$1,399
for 7 nights, 1 room
AU$200 per night
includes taxes & fees
The Pistachio Room at TPH - Boston
Private kitchen
Exterior detail
Living area
Interior
Exceptional
(8 reviews)

3-bedroom 2 baths beautiful victorian with WiFi, AC

Boston

8% off
AU$6,476
for 7 nights, 1 apartment
AU$925 per night
includes taxes & fees
3-bedroom 2 baths beautiful victorian with WiFi, AC
Hallway between bedrooms, kitchen & bathroom
Living area
Living area
Dining
Exceptional
(11 reviews)

Comfy, Stylish Apt. Near Uni's, Driveway

Somerville

8% off
AU$5,159
for 7 nights, 1 apartment
AU$737 per night
includes taxes & fees
Comfy, Stylish Apt. Near Uni's, Driveway
Living area
Room
Interior
Dining
Exceptional
(45 reviews)

A Cozy 5BR Apartment near Harvard Square and MIT

Cambridge

5% off
AU$5,744
for 7 nights, 1 apartment
AU$821 per night
includes taxes & fees
A Cozy 5BR Apartment near Harvard Square and MIT
Overview
Private kitchen
Laundry in property
Living area
Exceptional
(52 reviews)

A beautiful 3BR Apartment near Harvard and MIT.

Cambridge

6% off
AU$4,159
for 7 nights, 1 apartment
AU$594 per night
includes taxes & fees
A beautiful 3BR Apartment near Harvard and MIT.
Room
Interior
Private kitchen
Interior
Exceptional
(28 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
AU$5,586
for 7 nights, 1 apartment
AU$798 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Private kitchen
Dining
Living area
Room
Very good
(10 reviews)

3-bedroom apartment in charming Boston/ Near Train

Boston

8% off
AU$5,032
for 7 nights, 1 apartment
AU$719 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train
Open Kitchen/Dining Area
Living area
Entrance/steps to apartment. Please note, steps required
Located on floor 2 of a classic Boston 1860's Rowhouse
Exceptional
(89 reviews)

Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!

Boston

8% off
AU$2,292
for 7 nights, 1 apartment
AU$327 per night
includes taxes & fees
Special! One of VRBO's Most Popular!! L@@K 1.5 miles to center of Attractions!
Terrace/patio
Room
Living area
Dining
Exceptional
(23 reviews)

Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass

Cambridge

15% off
AU$3,541
for 7 nights, 1 home
AU$506 per night
includes taxes & fees
Cozy Cambridge 2bed 2bath w/ Patio & Parking Pass
Interior
Interior
Exterior
Interior
Wonderful
(15 reviews)

Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches

Winthrop

8% off
AU$1,958
for 7 nights, 1 apartment
AU$280 per night
includes taxes & fees
Private 1BR Top-Floor Retreat • Free Parking • Boston, Logan & Beaches
Fort Hill Inn, Boston. Main Building forthillinn.com
Isabella Stewart Gardner Museum, Walking distance from Inn
Open Space with Doors available for privacy between Kitchen/ Bedroom
Room
Exceptional
(83 reviews)

Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center

Boston

8% off
AU$2,292
for 7 nights, 1 apartment
AU$327 per night
includes taxes & fees
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
Living area
Exterior detail
Interior
Dining
Wonderful
(6 reviews)

Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center

Boston

8% off
AU$3,797
for 7 nights, 1 apartment
AU$542 per night
includes taxes & fees
Fort Hill Inn-- 2 bedroom Duplex, With a touch of modernity! Minutes to Center
Newly Refreshed Kitchen, Compact Dishwasher in cabinet under Sink
Interior
Located on the adjacent Private way. Outdoor Deck for guest use.
Queen Bedroom #2 on Garden Level
Wonderful
(34 reviews)

Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!

Boston

8% off
AU$3,761
for 7 nights, 1 apartment
AU$537 per night
includes taxes & fees
Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!
Located on a quiet Private Way, In The Fort Hill neighborhood.
Main Building At 3 Centre Place( You will be staying at 2 centre Place)
Open City Loft with sleeper sofa
Newly Renovated interior of The Boston/Public Library
Exceptional
(85 reviews)

Fresh Modern City Loft Apt! Easy Access to the city!

Boston

8% off
AU$2,220
for 7 nights, 1 apartment
AU$317 per night
includes taxes & fees
Fresh Modern City Loft Apt! Easy Access to the city!
Room
Living area
Interior
Private kitchen
Exceptional
(19 reviews)

"Fort Hill Inn, Boston" Cozy Studio Suite, Eat in Kitchen, 5 minutes to Center

Boston

8% off
AU$2,171
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
"Fort Hill Inn, Boston" Cozy Studio Suite, Eat in Kitchen, 5 minutes to Center
Living area
Exterior detail
Interior
Outdoor dining
Exceptional
(24 reviews)

Charming 1BR w/ Fireplace Near Fenway & Longwood

Brookline

7% off
AU$2,592
for 7 nights, 1 apartment
AU$370 per night
includes taxes & fees
Charming 1BR w/ Fireplace Near Fenway & Longwood
Room
Private kitchen
Dining
Living area
Exceptional
(19 reviews)

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.

Medford

8% off
AU$2,811
for 7 nights, 1 apartment
AU$402 per night
includes taxes & fees
Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
Dining
Living area
Exterior detail
Private kitchen
Exceptional
(19 reviews)

Harvard, B.U. M.I.T. Fenway Park convenient comfortable & spacious 3BR apartment

Cambridge

8% off
AU$5,348
for 7 nights, 1 apartment
AU$764 per night
includes taxes & fees
Harvard, B.U. M.I.T. Fenway Park convenient comfortable & spacious 3BR apartment

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Explore the lakeside setting in Winchester

The wildlife and lake provide a pleasant backdrop to your holiday home in Winchester. This city is well-known for its football matches and bird watching. Fenway Park and Encore Boston Harbor are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Winchester

Do you want to discover top things to see and do in the city? Venture out of your holiday home and check out everything that makes Winchester a one-of-a-kind holiday spot. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Encore Boston Harbor (5.2 mi / 8.4 km)
  • LEGO® Discovery Center Boston (4.9 mi / 7.9 km)
  • Boston Marathon Finish Line (7.7 mi / 12.4 km)
  • New England Aquarium (7.8 mi / 12.6 km)
  • Harpoon Brewery (8.9 mi / 14.4 km)
  • Samuel Adams Brewery (9.7 mi / 15.6 km)

Exploring the natural landscape of Winchester

Whether you're looking for adventure or just want to take in the scenery, Winchester is a great place to get outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (7.6 mi / 12.3 km)
  • Boston Harbor (7.6 mi / 12.2 km)
  • Copley Square (7.7 mi / 12.4 km)
  • Boston National Historical Park (6.8 mi / 11 km)
  • Charles River Esplanade (7.2 mi / 11.7 km)
  • Commonwealth Avenue Mall (7.5 mi / 12.1 km)

Travelling to and around Winchester

Fly into Bedford, MA (BED-Laurence G. Hanscom Field), the closest airport, located 7.7 mi (12.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Boston, MA (BNH-Boston Harbor Seaplane Base), which is 8.4 mi (13.5 km) away.

If you'd rather travel by train, make your way to Winchester Station or Winchester Wedgemere Station to see more of the city.

Frequently asked questions

What is the best area to stay in Winchester when booking a holiday rental?
When considering a holiday rental in Winchester, Massachusetts, one of the best areas to explore is the charming town centre. This area is not only picturesque but also conveniently located, offering easy access to a variety of shops, cafes, and restaurants that reflect the local culture. In the town centre, you can enjoy attractions such as the beautiful Winchester Town Common, which is great for leisurely strolls or picnics, and the historic Winchester Public Library, a lovely spot to admire architecture and soak in some local history.Another delightful area to consider is the picturesque neighbourhood of Fells. Known for its scenic landscapes and outdoor activities, the Fells offers ample opportunities for hiking and enjoying nature, particularly at the nearby Middlesex Fells Reservation, which is a favourite among locals for walking trails and wildlife spotting.In terms of holiday rentals, Winchester boasts a variety of properties, from cosy homes to larger accommodations suitable for families or groups. This diversity allows visitors to find something that fits their needs perfectly.
What is the most popular type of holiday rental accomodation in Winchester?
In Winchester, apartments and cottages are the most popular types of holiday rental accommodations, with several options available throughout the area. The apartments are typically situated in charming neighbourhoods, offering modern amenities such as fully equipped kitchens, comfortable living spaces, and often laundry facilities. Many of these rentals also provide easy access to local parks and the picturesque town centre, where visitors can explore shops and dining options.Cottages in Winchester present a more traditional and homely experience, often featuring features like quaint gardens, outdoor seating areas, and rustic interiors that highlight the area's historic charm. These properties are ideal for families or groups seeking a peaceful retreat while still being within reach of Boston's vibrant attractions.
Are there any family house rentals in Winchester?
In Winchester, Massachusetts, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The town features charming neighbourhoods that offer spacious homes equipped with essential amenities like full kitchens, ample living areas, and outdoor spaces for kids to enjoy. Many properties also include conveniences such as Wi-Fi and laundry facilities, ensuring a comfortable stay for the whole family.Visitors will appreciate the close proximity to local parks, including the beautiful Wright-Locke Farm, which provides a fantastic environment for outdoor activities and family outings. Additionally, the town is near the scenic shores of Lake Cochituate, superb for those who enjoy water-based fun.
Are there any remote work holiday rentals in Winchester?
In Winchester, Massachusetts, there are several remote work holiday rentals available, making it a great choice for those needing to balance work and leisure. Many of the properties feature amenities conducive to productivity, such as dedicated workspaces or desks, high-speed internet from reliable third-party services, and free Wi-Fi access in the rooms. This ensures that guests can stay connected and work efficiently while enjoying their stay.The town itself is charming, with picturesque streets and a rich history, providing a pleasant backdrop for both work and relaxation. Nearby points of interest include the scenic Horn Pond and various local parks, great for unwinding after a productive day. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winchester?
In Winchester, popular holiday rental amenities typically include kitchens, allowing guests to prepare their own meals, and air conditioning for comfort during warmer months. Many units also feature coffee and tea makers, which are superb for a morning brew. A desk is often provided, suiting those who might need to work or study during their stay. Additionally, onsite parking is commonly available, making it convenient for travellers with their own vehicles.
When is the best time to visit Winchester for a holiday rental?
April is the most popular time to visit Winchester, Massachusetts, as the spring blooms bring the town to life. From April through June, the peak season attracts a steady stream of travellers looking to enjoy the mild weather and vibrant local culture. With temperatures reaching between 10 to 20 degrees Celsius, this is an ideal time for outdoor activities, including leisurely strolls around the picturesque town centre and visits to the nearby parks.In April, visitors can witness the beauty of the cherry blossoms and engage in various spring festivities that highlight the charm of Winchester. The pleasant climate makes it comfortable for sightseeing and exploring the historic sites, such as the Winchester Public Library and the beautiful Horn Pond.For those seeking a more budget-friendly option, consider planning your trip in November. While this month falls outside the bustling tourist season, it provides a unique opportunity to explore the town at a relaxed pace, with the added bonus of enjoying the crisp autumn air and the last remnants of fall foliage.Ultimately, the best time to book a holiday rental in Winchester hinges on your personal preferences. If you thrive in a vibrant setting filled with seasonal activities, April to June will suit you perfectly. Alternatively, if you appreciate a quieter experience amidst stunning autumn landscapes, November can be an equally rewarding choice.
What are the top attractions in Winchester?
In Winchester, Massachusetts, visitors can enjoy a variety of attractions that highlight the town's rich history and natural beauty. The Winchester Town Common is a lovely green space superb for a leisurely stroll or a picnic, surrounded by charming historic buildings. The nearby Horn Pond offers picturesque walking trails and opportunities for birdwatching, making it a favourite spot for nature enthusiasts.For those interested in history, the Winchester Historical Society provides insights into the town's past and often hosts events and exhibitions. The picturesque downtown area features quaint shops and cafes, ideal for a relaxing afternoon. Additionally, the nearby Middlesex Fells Reservation offers hiking trails and scenic views, attracting outdoor lovers from the surrounding regions.
Are all fees included in the Winchester holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winchester holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winchester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winchester holiday homes?
You can find great discounts on holiday homes in Winchester on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winchester holiday home booking on Stayz?
To find Winchester holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winchester?
A long-stay holiday home in Winchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winchester holiday home?
Book your Winchester holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winchester?
Prices for holiday homes in Winchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winchester to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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