Best Vacation Homes in Westwood
New
Apartment
2 Bedrooms
1 Bath
4 Guests
900 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $233/Night
7 Nights - US $1,629
House
10.0(1 Review)
3 Bedrooms
1 Bath
6 Guests
1302.43 ft²
- Balcony/Terrace
View
Pet Friendly- Parking
US $1,054/Night
7 Nights - US $7,379
Hotel
8.4(529 Reviews)
1 Bath
- Fireplace/Heating
Pool- Balcony/Terrace
Breakfast
US $306/Night
7 Nights - US $2,142
Apartment
10.0(71 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
US $107/Night
7 Nights - US $749
House
8 Bedrooms
5 Baths
20 Guests
8212.86 ft²
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
US $3,335/Night
7 Nights - US $23,345
Apartment
10.0(9 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $155/Night
7 Nights - US $1,082
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Parking
- Air Conditioner
Internet
US $243/Night
7 Nights - US $1,701
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
1 Guest
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $102/Night
7 Nights - US $717
Westwood Luxury Rentals
House
6 Bedrooms
8 Baths
16 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $7,399/Night
7 Nights - US $51,793
House
6 Bedrooms
6 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Air Conditioner
US $4,125/Night
7 Nights - US $28,878
New
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $2,395/Night
7 Nights - US $16,767
House
10.0(26 Reviews)
4 Bedrooms
4 Baths
12 Guests
6100 ft²
Private Pool- Fireplace/Heating
- Pool
Ocean View
US $1,937/Night
7 Nights - US $13,559
House
10.0(6 Reviews)
8 Bedrooms
5 Baths
20 Guests
8215 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,918/Night
7 Nights - US $13,429
New
House
4 Bedrooms
3 Baths
13 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $1,131/Night
7 Nights - US $7,917
House
3 Bedrooms
3 Baths
8 Guests
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,103/Night
7 Nights - US $7,720
New
House
3 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $1,048/Night
7 Nights - US $7,339
Westwood Pet Friendly Vacation Rentals
Cottage
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $874/Night
7 Nights - US $6,119
New
House
4 Bedrooms
2 Baths
8 Guests
3605.91 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $863/Night
7 Nights - US $6,039
US $172/Night
7 Nights - US $1,201
Apartment
9.8(7 Reviews)
4 Bedrooms
3 Baths
13 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $630/Night
7 Nights - US $4,410
Apartment
2 Bedrooms
1 Bath
4 Guests
8072.93 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $163/Night
7 Nights - US $1,139
House
9.6(28 Reviews)
4 Bedrooms
2 Baths
10 Guests
2440 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $641/Night
7 Nights - US $4,488
House
9.6(4 Reviews)
3 Bedrooms
1 Bath
6 Guests
1300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $533/Night
7 Nights - US $3,732
House
2 Bedrooms
3 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $709/Night
7 Nights - US $4,966
Westwood Large Vacation Homes
House
6 Bedrooms
7 Baths
14 Guests
8000 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $2,296/Night
7 Nights - US $16,070
US $2,147/Night
7 Nights - US $15,029
Why Choose Rent By Owner for your Westwood Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Westwood
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as the region offers different attractions and activities depending on the season, making it ideal to plan your vacation rentals in Westwood, Massachusetts, USA, accordingly.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, the region experiences warm weather ideal for enjoying outdoor activities and exploring local sights. It’s a popular time for visitors seeking pleasant temperatures and longer daylight hours.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Early Fall (September to October)
This season offers mild temperatures and vibrant foliage, making it an excellent time to visit here for those who prefer comfortable weather and scenic views. Accommodation demand tends to peak as travelers take advantage of the picturesque surroundings.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
The colder months see fewer visitors, creating a quieter atmosphere perfect for relaxing in your rental and enjoying the cozy ambiance of the area. This is also a great opportunity for more affordable rates on vacation rentals.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Early Spring (March to April)
As the region transitions from winter, the early spring offers fewer crowds and lower prices. Visitors can enjoy the changing scenery and prepare for the busy summer seasons ahead.
Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F
Weekly Weather Forecast for Westwood
How to Book Your Westwood Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Westwood
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor seating areas perfect for relaxing and dining al fresco amid the scenic surroundings.
- Benefit from well-maintained lawns or gardens that provide a peaceful space for outdoor activities.
- Take advantage of private patios or decks for entertaining guests or enjoying morning coffee.
- Make use of outdoor grills or barbecues to enhance your culinary experience during your stay.
- Explore nearby walking trails or paths that surround your accommodation, ideal for outdoor enthusiasts.
- Relax in outdoor lounge furniture designed for comfort while soaking up the fresh air.
- Access landscaped yards or courtyards that add to the charm and tranquility of your stay in this destination.
Top Attractions Around Westwood
What attractions are nearby?
Here, you can explore a variety of outdoor activities and local attractions that offer an authentic taste of the region’s natural beauty and cultural charm, all within easy reach of your vacation rentals in Westwood, Massachusetts.
Family Activities
- Blue Hills Reservation: Explore this expansive natural area with family-friendly trails, hiking opportunities, and scenic views perfect for outdoor activities in the region.
- Westwood Public Library: Engage your family in storytime sessions and educational programs designed to inspire and entertain children and teens alike within this welcoming community hub.
- Houghton Pond Recreation Area: Enjoy relaxing picnics, swimming, and gentle walks around the pond, making it an ideal spot for family outings close to your vacation rental.
- Theatre Company of Weston & Metrowest: Attend engaging live performances and cultural events that offer a fun and enriching experience for families in the area's artistic community.
Adult Activities
- Visit the Westwood Historical Society Museum: Explore the rich local history and discover artifacts that tell the story of this area's development over the years.
- Enjoy a round of golf at the Westwood Golf Course: Relax and practice your swing at this scenic course, offering a tranquil setting perfect for outdoor enthusiasts.
- Hike or bike along nearby conservation trails: Take advantage of the region's natural beauty by exploring well-maintained paths through wooded areas and open spaces.
- Experience local dining at cozy restaurants: Savor delicious cuisine in intimate eateries that showcase regional flavors and hospitality here in the area.
Westwood Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take advantage of the area’s diverse culinary scene by trying nearby restaurants and cafes to enjoy authentic flavors unique to this destination.
- Plan your outdoor activities: Make the most of your stay by visiting parks, walking trails, or recreational spots that showcase the natural beauty of the region.
- Discover convenient transportation methods: Research available transit options to easily navigate the area and maximize your time exploring local attractions.
- Book well in advance: Secure your preferred vacation rentals early to ensure you have a comfortable base from which to experience everything here has to offer.
Transportation Options
- Boston Logan International Airport: This major airport offers convenient domestic and international flights, making it easy for you to access the region from anywhere around the world.
- Massachusetts Bay Transportation Authority (MBTA): The local transit authority provides commuter rail, subway, and bus services that connect here with Boston and surrounding communities for hassle-free travel.
- Rental Car Services: Many rental agencies operate nearby, giving you flexible options to explore this destination at your own pace.
- Taxi and Ride-Sharing Services: Reliable taxi companies and ride-sharing options are readily available within the area to provide quick transportation solutions during your stay.
Local Customs Options
- Traditional American Hospitality: Locals here take pride in welcoming visitors with warm, friendly interactions that reflect the region’s inviting spirit.
- Community Events and Parades: Participating in seasonal celebrations and local parades offers a unique opportunity to experience the area's close-knit community.
- Respect for Local History: Visitors are encouraged to honor the area's historic sites and preservation efforts that maintain its charming character.
- Environmental Conservation: The region emphasizes eco-friendly practices and respectful outdoor activities, ensuring natural beauty is preserved for all.
Westwood Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Westwood?
There are a lot of options in Westwood. If you plan on staying in the Westwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Westwood:
- Contemporary Style And Comfort Convenient To Boston And Route 128
- Gorg 6KSF w lrg pool, sleeps 12, 4.5 baths, rec room w bar, pool table & gym.
- Lovely, bright 1st fl, 1bd, fully furnished and accessorized small apartment
- Lavish Boston Estate for Mid Term 31+ night Stays | Pool, 8 BR
- Cozy Private Garden Suite near Gillette Stadium,Boston/BBQ/Parking/Walk to Train
- Upper-Level Oasis- Ideal for 2026 World Cup visitors
- Charming 3rd floor private loft space
- Perfectly Located & Comfy Suite - FIFA World Cup Ready !
- Elegant 4BR/3BR Home w/Yard & 4 Parking in Dedham
- Norwood Luxe Suite- Pet friendly & Commuter friendly
2. Which vacation homes in Westwood are best for families?
If you are looking for a family-friendly vacation home in Westwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Westwood:
3. How many Rentbyowner vacation rentals are available in Westwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 49 in the Westwood area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Westwood.
4. What is the cancellation policy for bookings in this area?
The cancellation policy varies depending on the individual property listing. To ensure your plans are flexible, review the specific cancellation terms provided in the rental details or contact the property owner directly for more information.
5. How do I know if the vacation rental is available during my preferred dates?
Availability is updated regularly on the listing page. You can quickly check if your desired dates are open by entering them in the booking calendar or reaching out to the host for confirmation.
6. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning, service charges, or taxes are typically detailed in the listing. Always review the total cost breakdown before completing your reservation or contact the host for clarification.
7. Is it possible to make special requests or customize my stay?
Yes, many hosts accommodate special requests like early check-in or late check-out. Contact the property owner beforehand to discuss your needs and confirm availability.
8. What amenities are included in the vacation rentals here?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and parking. Check each listing’s amenities section or contact the owner to ensure your specific requirements are met.
Westwood Top Rated Vacation Rentals
Hotel
8.0(135 Reviews)
5 Baths
505.9 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $265/Night
7 Nights - US $1,858
House
10.0(4 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Private Pool
- Hot Tub
Spa- Fireplace/Heating
US $447/Night
7 Nights - US $3,128
New
Cottage
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,713/Night
7 Nights - US $11,989
