Westwood Luxury Rental

New
16 Guests 6 Bedrooms 8 Bathrooms
Group Friendly House
Unlock the Best Price
New
16 Guests 6 Bedrooms 6 Bathrooms
Pet Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Pet Friendly
US $4,125/Night For 7 Nights US $28,878
New
8212.86 ft² 20 Guests 8 Bedrooms 5 Bathrooms
Free Cancellation House
  • Fireplace/Heating
  • Pool
  • Parking
US $3,335/Night For 7 Nights US $23,345
10.0
Exceptional
(6 Reviews)
8215 ft² 20 Guests 8 Bedrooms 5 Bathrooms
Family Friendly House
  • Private Pool
  • Fireplace/Heating
  • Pool
US $2,355/Night For 7 Nights US $16,485
10.0
Exceptional
(25 Reviews)
6100 ft² 12 Guests 4 Bedrooms 4 Bathrooms
Ocean View House
  • Private Pool
  • Fireplace/Heating
  • Pool
US $1,988/Night For 7 Nights US $13,919
New
4 Guests 1 Bedroom 1 Bathroom
Couples Retreat Cottage
US $1,713/Night For 7 Nights US $11,989
New
8 Guests 3 Bedrooms 3 Bathrooms
Family Friendly House
  • Hot Tub
  • Fireplace/Heating
  • Balcony/Terrace
US $1,395/Night For 7 Nights US $9,768
New
1302.43 ft² 6 Guests 3 Bedrooms 1 Bathroom
Family Friendly House
  • Balcony/Terrace
  • View
  • Pet Friendly
US $1,054/Night For 7 Nights US $7,379
New
10 Guests 3 Bedrooms 3 Bathrooms
Pet Friendly House
  • Fireplace/Heating
  • Air Conditioner
  • Internet
US $1,048/Night For 7 Nights US $7,339
New
3595.15 ft² 8 Guests 1 Bedroom 2 Bathrooms
Free Cancellation House
  • Fireplace/Heating
  • Pet Friendly
  • Parking
US $863/Night For 7 Nights US $6,039
9.6
Exceptional
(5 Reviews)
13 Guests 4 Bedrooms 3 Bathrooms
Pet Friendly Apartment
  • Fireplace/Heating
  • Pet Friendly
  • Air Conditioner
US $697/Night For 7 Nights US $4,879
New
3600 ft² 8 Guests 4 Bedrooms 2 Bathrooms
Group Friendly House
US $615/Night For 7 Nights US $4,304

Why Choose Rent By Owner for your Westwood Luxury Rental?

What makes our Luxury Rental special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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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 Luxury Rental stay?

Planning your perfect getaway involves selecting the ideal time to visit this destination, as the region offers seasonal appeal that can enhance your experience when booking luxury rentals here through RentByOwner.com.

Peak Season Highlights

summer
Late Spring to Early Summer (May - June)

During this period, the area experiences warm and inviting weather, making it ideal for enjoying outdoor amenities at your luxury rental. The pleasant temperatures also enhance your exploration of local surroundings.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
autumn
Early Fall (September - October)

This season offers a comfortable climate with the beauty of fall foliage. It’s perfect for relaxing in high-end accommodations while taking advantage of the region’s scenic vistas.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

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Mid Winter (January - February)

The quiet winter months bring cooler temperatures, providing a peaceful retreat in your luxury rental. It’s an opportune time to enjoy cozy indoor comforts away from the crowds.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Late Autumn (November - December)

As the leaves fall, the region becomes less crowded, offering a tranquil environment. This is an excellent time for those seeking serenity and seasonal holiday charm at their premium accommodations.

Average Temperature Daytime: 45-55°F - Nighttime: 35-45°F

Weekly Weather Forecast for Westwood

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.

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 private outdoor spaces with beautifully landscaped gardens perfect for relaxing or entertaining.
  • Take advantage of spacious patios equipped with outdoor dining areas for meals al fresco.
  • Make the most of inviting outdoor fireplaces or fire pits to gather with loved ones during cooler evenings.
  • Benefit from well-maintained swimming pools or hot tubs that provide a luxurious way to unwind outside.
  • Relax on expansive decks or verandas offering scenic views of the surrounding area.
  • Utilize dedicated barbecue grills for hosting memorable cookouts in the fresh air.
  • Explore beautifully appointed outdoor seating areas designed for enjoying the region’s pleasant climate and natural beauty.
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Family Activities

  • Hopkinton State Park Enjoy a day of outdoor fun with swimming, kayaking, and picnicking in this scenic park just outside the area, perfect for family bonding.
  • Westwood Recreation Department Participate in family-friendly sports, arts, and cultural activities organized throughout the year to keep everyone engaged.
  • The Children's Museum in Nearby Areas Explore interactive exhibits and engaging programs designed specifically for children, making it a great educational outing during your stay.
  • Local Nature Trails Discover easy-to-navigate walking or biking trails around the region, ideal for family adventures immersed in nature's beauty.
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Adult Activities

  • Golfing: Enjoy a relaxing day on the links at one of the region's premier golf courses, perfect for unwinding and appreciating the scenic landscape.
  • Historical Tours: Explore local history through guided tours that highlight the area's rich cultural heritage and notable landmarks.
  • Fine Dining Experiences: Indulge in gourmet cuisine at upscale restaurants offering exquisite menus within this destination’s vibrant culinary scene.
  • Shopping Excursions: Discover boutique shops and high-end stores that cater to discerning tastes, providing a sophisticated shopping experience in the area.

Westwood Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Ideal Stay: Take advantage of local resources to find the perfect luxury rentals that match your preferences for comfort and style in this destination.
  • Explore Nearby Dining Options: Leverage the area's diverse culinary scene to enjoy exceptional dining experiences during your visit, enhancing your overall trip.
  • Schedule Relaxing Activities: Arrange leisure activities close to your accommodation to maximize relaxation and convenience while exploring the region.
  • Connect with Local Services: Utilize trusted local services for transportation, concierge, or special requests to ensure a seamless and enjoyable stay in this area.

Transportation Options

  • Westwood MBTA Station This nearby transit hub provides convenient commuter rail services to downtown Boston and beyond, making it easy for you to explore the region without the hassle of driving.
  • Personal Vehicles Renting or using your own car offers flexible access to the area’s luxury rentals and other attractions, with ample parking available for your convenience.
  • Taxi and Rideshare Services Popular rideshare options like Uber and Lyft operate frequently here, providing a reliable and comfortable way to navigate the region in style.
  • Bike Rentals For an eco-friendly and active option, local bike rental services let you enjoy scenic rides throughout the neighborhood at your own pace.

Local Customs Options

  • Seasonal Harvest Festivals: Celebrated with community-wide events, these festivals highlight local produce and traditional foods, offering an authentic taste of the area's agricultural heritage.
  • Historical Preservation Ceremonies: Respect for history is evident through annual ceremonies and reenactments that honor the region’s rich past and cultural legacy.
  • Local Art Exhibitions: Art showcases often feature works inspired by the region's natural beauty and history, providing an enriching experience for visitors seeking cultural connections.
  • Community Service Events: Engaging in neighborhood cleanup days and charity runs reflects a strong sense of community pride, making your visit here more meaningful.

Westwood Luxury Rental Frequently Asked Questions

2. How many Luxury Rentals are available in Westwood?

Currently, the total number of properties listed by RBO in 2026 is over 44 in the Westwood area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Luxury Rentals in Westwood. 

3. What is the cancellation policy for booking luxury rentals in Westwood?

The cancellation policy varies depending on the property listing. It is recommended to review the specific details on the listing page or contact the owner directly to understand the applicable cancellation terms.

4. Are there any additional fees I should be aware of when booking in this area?

Additional fees such as cleaning charges, service fees, or local taxes may apply. These are typically detailed on the property listing, so reviewing the listing information or reaching out to the host will provide clarity.

5. How can I ensure my reservation in Westwood will be confirmed and secure?

Reservations are generally confirmed once payment is processed and the property owner approves your booking. For added assurance, communicate with the host directly through the platform to confirm availability and booking details.

6. What amenities are included in luxury rentals here?

Luxury rentals often come with high-end amenities such as modern kitchens, premium furnishings, private outdoor spaces, and tech features. Specific amenities vary by property, so please check the listing details for exact offerings.

7. Is there a minimum stay requirement for luxury accommodations in this destination?

Minimum stay requirements differ by property and season. It’s best to review the individual listing or contact the owner to confirm any stay length restrictions before making a reservation.

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  • Parking
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US $265/Night For 7 Nights US $1,858
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  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $250/Night For 7 Nights US $1,747
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4 Guests 1 Bedroom 1 Bathroom
Couples Retreat Apartment
  • Fireplace/Heating
  • Parking
  • Air Conditioner
US $246/Night For 7 Nights US $1,720
9.2
Exceptional
(55 Reviews)
1300 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Kitchen
  • Parking
US $233/Night For 7 Nights US $1,634
8.0
Excellent
(549 Reviews)
398.26 ft² 1 Bathroom
Family Friendly Hotel
  • Fireplace/Heating
  • Pet Friendly
  • Parking
US $228/Night For 7 Nights US $1,594
New
900 ft² 4 Guests 2 Bedrooms 1 Bathroom
Family Friendly Apartment
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $201/Night For 7 Nights US $1,410
New
2 Guests 1 Bedroom 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
US $193/Night For 7 Nights US $1,353