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Weston vacation rentals

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August 2025

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Scroll through and select from vacation rentals in Weston to find one that's perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the amenities you need and want, which might include parking and a fireplace. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Weston

Showing deals for:Nov 14 - Nov 21

Exceptional

(77 reviews)

Beautiful Boston Brownstone!

Boston, MA

10% off

includes taxes & fees

Exceptional

(63 reviews)

West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

Boston, MA

19% off

includes taxes & fees

Exceptional

(14 reviews)

Luxury Modern Home - Family Friendly Close to Boston and Gillete Stadium!

Dedham, MA

10% off

includes taxes & fees

Exceptional

(22 reviews)

4BR, 4Bath Dream Home Experience: sauna, hot tub, pool. Explore Boston in Style!

Newton, MA

10% off

includes taxes & fees

Front view of the single house builded on the hill in a nice street of Boston

Exceptional

(43 reviews)

Terrific vacation house only 4.5 miles away from downtown Boston

Boston, MA

13% off

includes taxes & fees

Exceptional

(10 reviews)

Award-winning Queen size bedroom suite near Harvard, MIT at Central SQ Cambridge

Cambridge, MA

5% off

includes taxes & fees

Wonderful

(14 reviews)

A NEW ENGLAND ORIGINAL, 3-bedroom Colonial farmhouse, 3 min. from I90 & I95.

Weston, MA

5% off

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Weston

A NEW ENGLAND ORIGINAL, 3-bedroom Colonial farmhouse, 3 min. from I90 & I95.

Sleeps 8 · 3 bedrooms · 2+ bathrooms

Top rated rentals - Weston

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Find out more about Weston

Why visit Weston

Cultural Exploration: Discover a rich blend of historic sites and modern universities, perfect for culture enthusiasts.
Outdoor Activities: Enjoy beautiful surroundings with ample opportunities for hiking and outdoor recreation.
Vibrant Arts Scene: Immerse yourself in the local arts community with galleries and performances nearby.
Family-Friendly Atmosphere: Experience a welcoming environment, ideal for visitors of all ages.
Diverse Accommodation: Choose from cozy apartments to spacious homes tailored to your vacation needs.

Popular types of accommodation in Weston

Welcome to Weston, where you’ll find an array of vacation rentals tailored to your needs. Whether you're seeking a cozy apartment, a spacious private vacation home, or a modern condo, there’s something for everyone. From Weston apartments to Weston MA homes for rent, our platform ensures you find the perfect accommodation for your getaway. Explore your options and enjoy your stay in this charming community!

Apartments: The top choice among visitors to Weston, offering convenience and a home-like atmosphere.
Houses: A close second, these homes provide spacious living suitable for families or groups.
Condos: A popular option for those seeking modern amenities and a community vibe.
House Boats: Unique accommodations that offer a relaxing stay on the water.
Cottages: A charming retreat ideal for a peaceful getaway in nature.**

Top attractions in Weston

Weston, Massachusetts, offers a delightful mix of cultural and outdoor experiences for tourists. Whether you're interested in historic or modern universities, or art museums, there's plenty to explore. This charming town is perfect for anyone seeking a rich city experience, allowing visitors to immerse themselves in the local culture while enjoying the beautiful surroundings. Make sure to take advantage of all that Weston has to offer during your vacation!

Fenway Park: A historic sports stadium steeped in baseball culture, Fenway Park is renowned for its iconic Green Monster and vibrant atmosphere. It's an essential stop for sports enthusiasts, offering a glimpse into American sports history.
Harvard University: As the oldest institution of higher education in the United States, Harvard boasts stunning architecture and rich cultural heritage. Explore its beautiful campus and soak in the academic atmosphere.
Boston College: A modern university that seamlessly blends tradition with contemporary city vibes. Its picturesque campus offers a vibrant community and engaging events, perfect for immersing yourself in student life.

Things to do recommended for couples

For a romantic getaway in Weston, consider a night of live music at the House of Blues in Boston, just 17.7km away. Enjoy wine tasting at Turtle Creek Winery, only 6.4km away, or dine at The Russell House, 12.9km away, for a delightful evening filled with romance.

Things to do recommended for families

During your family vacation in Weston, Massachusetts, explore the sports vibes at Agganis Arena, enjoy adventure at Fun and Games Family Entertainment Center, and relax at Cat Rock Park, all offering memorable experiences for the whole family.

Things to do recommended for groups

Groups visiting Weston, Massachusetts can enjoy shopping at Harvard Square, just 14.5km away, or catch a film at the charming Coolidge Corner Theatre, also 14.5km distant. Don't miss a visit to American Girl Boston, located 9.7km from Weston, for a delightful shopping experience.

What do I need to keep in mind when booking a vacation in Weston

When you're planning a trip—whether with a group, family, pets, or for an extended stay—it's important to prioritize your needs in the booking process. Here are some helpful tips for booking on Vrbo.

Traveling to Weston with a group: Take into account the number of bedrooms you'll require, along with features like a complete kitchen or outdoor space for group gatherings. Thankfully, you can easily apply filters for all of these options and more on Vrbo.
Traveling to Weston with young kids: Traveling with young kids can be quite the adventure. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, keeping in mind your closeness to family-friendly attractions can enhance your experience.
Taking your pets with you to Weston: For many families, a vacation isn't truly fulfilling without their furry companions. If you relate to this, explore Vrbo properties that welcome pets. The majority of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
Planning for a long term stay visiting Weston: If you're searching for vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search!

Where to stay in Weston

Weston, Massachusetts, is a charming destination perfect for culture enthusiasts and outdoor lovers alike. Explore the family-friendly atmosphere and vibrant arts scene while enjoying prime locations within walking distance of top attractions. Nearby cities offer a mix of urban energy and friendly locals, creating a memorable experience for all visitors. Whether you're here for business or leisure, Weston and its surrounding areas promise a delightful getaway.

Waltham: Located 6.4km from Weston, Waltham is a vibrant city that offers a rich blend of culture and family-friendly experiences. It's renowned for its educational institutions, including historic and modern colleges, making it a great spot for those interested in academia. The city boasts a lively music scene, with numerous concerts and events throughout the year. Visitors can enjoy shopping at local malls and exploring the historic stadiums that add to Waltham's charm. This city is perfect for those looking to immerse themselves in a dynamic urban environment.
Wayland: Just 4.8km from Weston, Wayland is a picturesque city ideal for outdoor enthusiasts and those seeking a romantic getaway. The stunning scenery includes beautiful lakes and beaches, making it perfect for leisurely strolls or picnics. Wayland is also home to several recreational areas where you can engage in various outdoor activities. The local shopping centres provide a delightful experience, blending convenience with local charm. A visit to the nearby national state park offers opportunities for hiking and exploring nature, ensuring a memorable stay.
Banks Square: Situated 4.8km from Weston, Banks Square is a lively neighbourhood that combines culture, sports, and outdoor activities. With its array of educational venues, including historic colleges, this area is steeped in tradition. Sports enthusiasts will appreciate the local stadium and historic sports venues that host various events. Entertainment options abound, from casinos to music concerts, ensuring there's something for everyone. The charm of Banks Square lies in its vibrant community and diverse attractions, making it a must-visit for any traveller.

Best time to go to Weston

If you're planning a trip to Weston, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and July, while off-peak times, like November to January tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	28.4°F (-2.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	29.8°F (-1.2°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
April	47.7°F (8.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	58.3°F (14.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	66.4°F (19.1°C)	Light Rain	Mostly Sunny	Average	Average
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Average	Average
September	65.3°F (18.5°C)	Light Rain	Mostly Sunny	Average	Average
October	54.5°F (12.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	43.2°F (6.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	34.7°F (1.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average

Booking with Vrbo is simple

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can make a significant difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that meets your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo's groundbreaking Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, and manage your travel arrangements with ease. You can easily access the properties you've saved or booked in your Potential, Upcoming, or Current Trips sections. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

The riverside setting of Weston is ready to explore

The riverfront and island views create a pretty picture of Weston. Renowned for its basketball games, university setting and camping, this city welcomes all visitors. Fenway Park and TD Garden are just a couple of the must-sees in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Weston

Do you want to discover attractions to see while you're in town? Venture out of your cozy vacation rental and experience everything that makes Weston a fun place to get away. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

New England Aquarium (13 mi / 20.8 km)
Encore Boston Harbor (12.1 mi / 19.5 km)
Massachusetts Horticultural Society's Gardens at Elm Bank (6.2 mi / 10 km)
Samuel Adams Brewery (10.9 mi / 17.5 km)
Boston Marathon Finish Line (11.5 mi / 18.5 km)
Franklin Park Zoo (11.7 mi / 18.9 km)

Exploring the natural features in Weston

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Weston is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

Boston Common (12.1 mi / 19.5 km)
Copley Square (11.6 mi / 18.7 km)
Walden Pond (5.4 mi / 8.6 km)
Cochituate State Park (5.5 mi / 8.9 km)
Chestnut Hill Reservoir (7.7 mi / 12.4 km)
Back Bay Fens (10.8 mi / 17.4 km)

Transportation options to and around Weston

Fly into Bedford, MA (BED-Laurence G. Hanscom Field), the closest airport, located 6.8 mi (10.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Norwood, MA (OWD-Norwood Memorial), which is 14 mi (22.5 km) away.

If you're traveling by train, Weston Kendal Green Station, Weston Hastings Station and Weston Silver Hill Station are the main stations that serve the city.

Frequently asked questions

What is the best area to stay in Weston when booking a vacation rental?

When considering a vacation rental in Weston, Massachusetts, a popular area to stay is near the town centre, which exudes charm and convenience. This neighbourhood offers a delightful mix of quaint shops, lovely restaurants, and easy access to local parks, making it an ideal base for exploring the area. You'll find a variety of properties available, from comfortable family homes to more luxurious options, suiting different tastes and budgets.

How much does it cost to rent a vacation home in Weston?

Prices for vacation rentals in Weston 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. Vrbo offers something for every taste and budget, from affordable rentals in Weston to more spacious homes.

Are there any discounts for Weston vacation house rentals?

You can find great discounts on house rentals in Weston on Vrbo, 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.

What is the most popular type of vacation rental accomodation in Weston?

In Weston, vacation houses are the predominant type of rental accommodation, with several available throughout the area. These homes typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many houses also feature private gardens and outdoor spaces, great for relaxing after a day of exploring the local parks or nearby attractions like the historic town centre.

Are there any family house rentals in Weston?

In Weston, Massachusetts, there are several family-friendly house rentals available, suiting those looking for spacious rooms. The area is known for its serene suburban atmosphere, making it a great choice for families. Many of these homes feature ample living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.

Can I rent a vacation home with a pool or hot tub in Weston?

In Weston, Massachusetts, there are several vacation homes available for rent that feature pools or hot tubs. This affluent suburb offers a serene environment with easy access to Boston and its surrounding areas. Many of these properties include amenities such as private swimming pools, hot tubs, expansive backyards, and well-equipped kitchens, making them ideal for families or groups looking to relax and unwind. Additionally, some rentals may provide outdoor spaces for entertaining, as well as comfortable living areas for leisure time indoors.

Can I find long-stay vacation rentals in Weston?

A long-stay vacation rental in Weston 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Are there pet-friendly house rentals in Weston?

In Weston, Massachusetts, there are several pet-friendly house rentals available for travellers looking to enjoy a comfortable stay. Many of these properties offer amenities such as spacious backyards, modern kitchens, and cosy living areas, making them ideal for families or groups travelling with pets.

The town is known for its picturesque landscapes and access to outdoor activities, with nearby parks like the scenic Weston Town Forest. This area features walking trails that are great for leisurely strolls with pets. Additionally, the nearby Sudbury River provides opportunities for kayaking and nature walks, allowing pet owners to explore the beautiful surroundings.

Are there any remote work vacation rentals in Weston?

In Weston, Massachusetts, there are several vacation rentals suitable for remote work. These properties often come equipped with dedicated workspaces, including desks and office chairs, ensuring that you have a comfortable environment to focus on your tasks. High-speed Wi-Fi is typically available, allowing for seamless connectivity during your work hours. Additionally, many rentals feature amenities such as safes for securing valuables, and some may even offer outdoor spaces to enjoy a break while taking in the lovely surroundings. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.

Are there any Weston vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in Weston 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 on Vrbo 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.

When is the best time to visit Weston for a vacation rental?

April marks the most popular time to visit Weston, Massachusetts, as the spring blooms breathe life into the area. The peak season spans from March to May, making it an ideal period for those seeking outdoor activities and charming local experiences. With temperatures typically ranging from 10 to 18 degrees Celsius, the weather is superb for leisurely strolls through the picturesque parks and gardens.

During this vibrant spring season, visitors can enjoy various activities, such as exploring the scenic trails or participating in local events that celebrate the community's rich history and culture. The delightful sights and sounds of nature provide a stunning backdrop for your adventures, making it a comfortable time for sightseeing.

If you're considering a more budget-friendly option, visiting in December can offer a great experience. The vacation season transforms Weston into a winter wonderland, with festive decorations and a warm community spirit. While the temperatures can drop to around zero degrees Celsius, embracing the winter charm and partaking in vacation festivities can be truly rewarding.

How early should I book a Weston vacation rental?

Book your Weston vacation rental 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 Vrbo booking and occupancy data for 2024 stays.

Can I change or cancel my Weston home rental booking on Vrbo?

To find Weston vacation rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

Are all fees included in the Weston vacation rental prices shown on Vrbo?

Vrbo 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.