Westwood holiday rentals

We found 1,111 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Westwood that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll have the amenities that you expect and more, such as parking and air conditioning. What you'll find is a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Westwood

Showing deals for:25 Dec - 1 Jan

Private kitchen
Interior
Interior
Exceptional
(96 reviews)

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

Boston

8% off
AU$16,761
for 7 nights, 1 home
AU$2,394 per night
includes taxes & fees
Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston
Interior
Exterior detail
Outdoor dining
Interior
Exceptional
(6 reviews)

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

Newton

9% off
AU$25,210
for 7 nights, 1 home
AU$3,601 per night
includes taxes & fees
Luxury Tuscan style villa just few miles from downtown Boston .Newton Reg #24-17
Exterior
Terrace/patio
Private kitchen
Room
Exceptional
(34 reviews)

Lovely Studio Walk to Wellesley and Babson College

Wellesley

8% off
AU$3,039
for 7 nights, 1 home
AU$434 per night
includes taxes & fees
Lovely Studio Walk to Wellesley and Babson College
Room
Interior
Interior
Interior
Exceptional
(21 reviews)

Modern home-like 3BR2BA Retreat/Minutes to T

Boston

8% off
AU$5,876
for 7 nights, 1 home
AU$839 per night
includes taxes & fees
Modern home-like 3BR2BA Retreat/Minutes to T
Interior
Living area
Private kitchen
Interior
Wonderful
(19 reviews)

Newly Renovated Modern Retreat l Near T

Boston

5% off
AU$5,785
for 7 nights, 1 apartment
AU$826 per night
includes taxes & fees
Newly Renovated Modern Retreat l Near T
Interior
Private kitchen
Living area
Dining
Wonderful
(24 reviews)

Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2

Boston

8% off
AU$5,648
for 7 nights, 1 apartment
AU$807 per night
includes taxes & fees
Brand-new Modern 4BR Boston Comfortable Apartment w/Parking Pet-Friendly - 80/2
Stainless steel kitchen appliances. (Old Table)
Backyard
BPL Egleston Square library branch
Living room
Exceptional
(69 reviews)

2 bedrooms with air-conditioning, parking, laundry, WiFi near Sam Adams & subway

Boston

5% off
AU$3,502
for 7 nights, 1 apartment
AU$500 per night
includes taxes & fees
2 bedrooms with air-conditioning, parking, laundry, WiFi near Sam Adams & subway
Private kitchen
Spacious 4 BR home for groups. Perfect for relaxing and gathering together
Outdoor dining
Dining
Exceptional
(12 reviews)

4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train

Boston

8% off
AU$7,384
for 7 nights, 1 apartment
AU$1,055 per night
includes taxes & fees
4BR Near Downtown Boston Private Driveway Parking & 1-Min Walk to Train
Private kitchen
Interior
Dining
Room
Very good
(6 reviews)

6BR3BA w Parking Near T I Foosball & Family Space

Boston

8% off
AU$6,959
for 7 nights, 1 apartment
AU$994 per night
includes taxes & fees
6BR3BA w Parking Near T I Foosball & Family Space
Room
Living area
Interior
Living area
Exceptional
(78 reviews)

The Pistachio Room at TPH - Boston

Boston

7% off
AU$1,397
for 7 nights, 1 room
AU$200 per night
includes taxes & fees
The Pistachio Room at TPH - Boston
Dining
Room
Living area
Interior
Exceptional
(45 reviews)

A Cozy 5BR Apartment near Harvard Square and MIT

Cambridge

7% off
AU$5,624
for 7 nights, 1 apartment
AU$803 per night
includes taxes & fees
A Cozy 5BR Apartment near Harvard Square and MIT
Room
Private kitchen
Overview
Laundry in property
Exceptional
(52 reviews)

A beautiful 3BR Apartment near Harvard and MIT.

Cambridge

6% off
AU$4,152
for 7 nights, 1 apartment
AU$593 per night
includes taxes & fees
A beautiful 3BR Apartment near Harvard and MIT.
Interior
Interior
Room
Private kitchen
Exceptional
(28 reviews)

3BR2BA Retreat - 2min to Savin Hill Station

Boston

8% off
AU$5,577
for 7 nights, 1 apartment
AU$797 per night
includes taxes & fees
3BR2BA Retreat - 2min to Savin Hill Station
Room
Dining
Living area
Private kitchen
Very good
(10 reviews)

3-bedroom apartment in charming Boston/ Near Train

Boston

8% off
AU$5,024
for 7 nights, 1 apartment
AU$718 per night
includes taxes & fees
3-bedroom apartment in charming Boston/ Near Train
Entrance/steps to apartment. Please note, steps required
Living area
Interior
Open Kitchen/Dining Area
Exceptional
(89 reviews)

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

Boston

8% off
AU$2,288
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!
Private kitchen
Interior
Living area
Outdoor dining
Exceptional
(30 reviews)

Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train

Boston

7% off
AU$2,497
for 7 nights, 1 apartment
AU$357 per night
includes taxes & fees
Cozy 2-bedroom apartment in charming Boston with WiFi, AC. Commuter train
Exterior
Living area
Dining
Room
Exceptional
(34 reviews)

Waterfront Lakehouse near Gillette Stadium, central to Boston & Providence

Wrentham

16% off
AU$6,040
for 7 nights, 1 home
AU$863 per night
includes taxes & fees
Waterfront Lakehouse near Gillette Stadium, central to Boston & Providence
Fort Hill Inn, Boston. Main Building forthillinn.com
Isabella Stewart Gardner Museum, Walking distance from Inn
Modern with nice Historic Details, Original Decorative Marble Fireplace
Room
Exceptional
(83 reviews)

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

Boston

8% off
AU$2,288
for 7 nights, 1 apartment
AU$327 per night
includes taxes & fees
Special!!excellent, Sunny! Duplex!! Pvt! Condo! 1.5 Miles to Center
Quartz Countertop
Interior
Dining
Sunroom
Exceptional
(14 reviews)

Spacious luxury home, 22 min from Boston and 20 min from Gillette Stadium.

Stoughton

21% off
AU$8,470
for 7 nights, 1 home
AU$1,210 per night
includes taxes & fees
Spacious luxury home, 22 min from Boston and 20 min from Gillette Stadium.
Living area
Exterior detail
Open Kitchen
Dining
Wonderful
(6 reviews)

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

Boston

8% off
AU$3,791
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
Queen Bedroom #2 on Garden Level
Interior
Open Dining with Galley Kitchen
Located on the adjacent Private way. Outdoor Deck for guest use.
Wonderful
(34 reviews)

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

Boston

8% off
AU$3,755
for 7 nights, 1 apartment
AU$536 per night
includes taxes & fees
Fort Hill Inn, Boston *Sunny* 2 bed Duplex, Spacious! ! Minutes to Center!!
Open City Loft with sleeper sofa
Main Building At 3 Centre Place( You will be staying at 2 centre Place)
Located on a quiet Private Way, In The Fort Hill neighborhood.
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$2,216
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
Exterior detail
Private kitchen
Exceptional
(19 reviews)

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

Boston

8% off
AU$2,168
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
Private kitchen
Stairs to Apartment - We Shovel for You!
Outdoor dining
Living Room - Your Home Away from Home
Exceptional
(24 reviews)

Large 5-Bed Modern Family Retreat with Kitchen & Free Parking Near Boston!

Boston

5% off
AU$1,941
for 7 nights, 1 apartment
AU$277 per night
includes taxes & fees
Large 5-Bed Modern Family Retreat with Kitchen & Free Parking Near Boston!

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Westwood getaway

Enjoy the monuments and other features of Westwood. This city's restaurants, shopping and bird watching draw many visitors. Gillette Stadium and Fenway Park are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Westwood

Are you hoping to find things to do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Westwood a fun place to get away to. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Encore Boston Harbor (14.8 mi / 23.8 km)
  • The Skating Club of Boston (2.8 mi / 4.5 km)
  • Blue Hills Ski Area (5.5 mi / 8.9 km)
  • Massachusetts Horticultural Society's Gardens at Elm Bank (6.2 mi / 10 km)
  • Blue Hills Reservation (7.3 mi / 11.8 km)
  • Granite Links Golf Club (9.3 mi / 15 km)

Exploring the natural landscape of Westwood

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Westwood is a great place to spend some time outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Boston Common (12.7 mi / 20.4 km)
  • Copley Square (12.1 mi / 19.4 km)
  • Boston Harbor (13.6 mi / 21.9 km)
  • Arnold Arboretum (7.8 mi / 12.5 km)
  • Cochituate State Park (10.2 mi / 16.4 km)
  • Back Bay Fens (11.3 mi / 18.1 km)

How to get to and around Westwood

The nearest airport is in Norwood, MA (OWD-Norwood Memorial), located 3 mi (4.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Boston, MA (BNH-Boston Harbor Seaplane Base), which is 14.3 mi (23 km) away.

If you're travelling by train, the main station is Westwood Islington Station.

Frequently asked questions

What is the best area to stay in Westwood when booking a holiday rental?
When considering a holiday rental in Westwood, Massachusetts, the area around the town centre is an excellent choice. This neighbourhood offers a charming suburban atmosphere with convenient access to a variety of amenities. One of the standout attractions nearby is the picturesque Westwood Town Common, a lovely green space great for leisurely strolls or picnics. Additionally, the area is close to the Westwood Public Library, which not only serves as a great resource but also hosts various community events throughout the year.Another appealing neighbourhood is the one surrounding the nearby University Avenue, where you'll find a selection of dining options and shops. This area is particularly convenient for those looking to explore the local culture and enjoy a taste of the community's vibrant lifestyle. Westwood boasts a modest number of properties available for holiday rentals, providing a range of options to suit different preferences and budgets.
What is the most popular type of holiday rental accomodation in Westwood?
In Westwood, holiday houses are a popular choice, with several available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many properties also include outdoor spaces such as gardens or patios for relaxing after a day of exploring. Additionally, apartments can be found in the area, offering a more compact alternative for travellers seeking a cozy feel.
Are there any family house rentals in Westwood?
In Westwood, Massachusetts, there are several family-friendly house rentals available, providing a range of options for those travelling with children. This charming suburb features spacious homes that often include large living areas, fully equipped kitchens for preparing family meals, and well-maintained outdoor spaces where kids can play. Many properties also come with amenities like Wi-Fi and laundry facilities, ensuring a comfortable and convenient stay for families.The locale is close to several parks, such as the picturesque Hale Reservation, which offers trails for hiking and scenic spots for picnicking. Families can also enjoy the nearby Legacy Place, a shopping and dining destination that features various restaurants and entertainment options.
Are there pet-friendly house rentals in Westwood?
In Westwood, Massachusetts, there are several pet-friendly house rentals available, making it an inviting option for travellers with furry companions. The area is known for its suburban charm and access to green spaces, which are great for outdoor activities with pets. Many of the holiday homes feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, ensuring a relaxing stay for both guests and their pets.Additionally, Westwood is conveniently located near several parks, including the picturesque Hale Reservation, which offers trails and open spaces for walking and exploring.
Are there any remote work holiday rentals in Westwood?
In Westwood, Massachusetts, there are several options for remote work holiday rentals, with around 12 properties available. Many of these accommodations are well-equipped to cater to the needs of remote workers, featuring amenities such as high-speed internet and dedicated workspaces with desks and chairs. Some rentals also provide free Wi-Fi throughout the property, ensuring a seamless online experience.The town itself offers a pleasant suburban atmosphere, making it a great place to balance work and leisure. Nearby, you'll find local parks and recreational areas, great for a break from work. Additionally, Westwood is conveniently located near public transport links, providing easy access to Boston and its surrounding areas for those looking to explore the city during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Westwood?
In Westwood, popular rental amenities often include balconies, allowing guests to enjoy the outdoors from the comfort of their accommodation. Many properties feature coffee and tea makers for convenience, alongside onsite parking to alleviate any concerns about vehicle storage. Additionally, rentals typically come with decks or patios, providing private spaces for relaxation or dining al fresco.
When is the best time to visit Westwood for a holiday rental?
April is the most popular time to visit Westwood, Massachusetts, as spring begins to bloom and the area comes alive with vibrant colours and outdoor activities. The peak season runs from February to April, attracting visitors eager to enjoy the mild weather and partake in local events. This time of year is superb for those seeking to explore the scenic parks, enjoy leisurely strolls, and participate in community festivities.As temperatures rise to a comfortable range of 5 to 15 degrees Celsius, April offers an ideal climate for outdoor adventures, including picturesque walks through the many trails and enjoying the local flora. The sense of renewal in the air creates a delightful atmosphere for sightseeing and relaxing in the beautiful surroundings.For travellers interested in a more budget-friendly option, November presents an excellent choice. During this quieter month, you can enjoy the peacefulness of Westwood while still appreciating the autumn scenery. The crisp air and colourful leaves create a stunning backdrop for outdoor explorations and photography.Ultimately, the best time to book a holiday rental in Westwood depends on your preferences.
What are the top attractions in Westwood?
In Westwood, Massachusetts, visitors can enjoy a range of attractions that highlight the area's natural beauty and community spirit. The picturesque Westwood Town Common is a lovely spot for leisurely strolls and community events, often bustling with local activities. Nearby, the Westwood Historical Society presents an opportunity to delve into the town's rich history through various exhibits and preserved sites.For outdoor enthusiasts, the Hale Reservation offers extensive trails for hiking, as well as opportunities for canoeing and kayaking in the warmer months. This vast area is superb for family outings and nature exploration. The nearby Legacy Place is a vibrant shopping and dining destination, featuring a mix of retailers and restaurants, making it ideal for a day out.
Are all fees included in the Westwood 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 Westwood holiday homes with parking?
Stayz offers a wide selection of holiday homes in Westwood 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 Westwood holiday homes?
You can find great discounts on holiday homes in Westwood 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 Westwood holiday home booking on Stayz?
To find Westwood 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 Westwood?
A long-stay holiday home in Westwood 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 Westwood holiday home?
Book your Westwood 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 Westwood?
Prices for holiday homes in Westwood 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 Westwood 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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