Discover Your Perfect Fenway–Kenmore Vacation Homes

Best Vacation Homes in Fenway–Kenmore

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8.6 (330 Reviews)
Apartment
Maverick Suites at 28 Fenway
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
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Fenway–Kenmore Luxury Rentals

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Fenway–Kenmore Pet Friendly Vacation Rentals

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9.3 (2804 Reviews)
Hotel
The Verb Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
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Why Choose Rent By Owner for your Fenway–Kenmore Vacation Rental Homes?

What makes our Vacation Rentals 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.

Popular Areas for Fenway–Kenmore Vacation Rentals

Where are the best neighborhoods to stay in Fenway–Kenmore?

When selecting a neighborhood to stay in within Fenway–Kenmore, Boston, Massachusetts, you’ll enjoy the convenience of a vibrant area known for its rich cultural scene and accessibility. This neighborhood offers a blend of historic charm and modern amenities, making it an ideal base for exploring Boston’s attractions. Whether you're looking for proximity to renowned sports venues or a lively local atmosphere, staying here ensures you’re at the heart of it all. Discover the ease of exploring Boston from your well-located vacation rentals in this dynamic part of the city.

Back Bay

In this area, you'll find a vibrant neighborhood known for its historic architecture and lively shopping streets. It's an ideal location to explore Boston's cultural scene while enjoying the comfort of well-appointed vacation rentals nearby.

View 278+ Rentals in Back Bay

Allston

This neighborhood offers a youthful atmosphere with a thriving arts and music scene, making it perfect for travelers seeking an energetic, local experience. Here, comfortable vacation rentals place you close to popular cafes and entertainment venues.

View 53+ Rentals in Allston

South End

Known for its elegant brownstones and diverse culinary options, this destination provides a refined yet welcoming environment. Staying here offers easy access to boutique shops and charming streets, ideal for relaxing exploration.

View 175+ Rentals in South End

Roxbury

This neighborhood combines rich history with a vibrant community atmosphere, offering authentic Boston experiences. Your choice of vacation rentals here ensures proximity to cultural landmarks and local hangouts.

View 84+ Rentals in Roxbury

Mission Hill

Perched on a hillside, this area provides stunning views and easy access to the region’s parks. It’s an excellent spot for travelers seeking peaceful surroundings with convenient routes to the city’s main attractions.

View 3442+ Rentals in Mission Hill

Shawmut

Famous for its historic sites and quaint neighborhood feel, Shawmut offers a quiet retreat within the city. Vacation rentals here give you a chance to enjoy local charm while being close to Boston's key destinations.

View 92+ Rentals in Shawmut

West Fens

Bordering the university district, this area is perfect for those interested in academic and cultural activities. Staying here grants easy access to educational institutions and the lively campus environment.

View 174+ Rentals in West Fens

Medical Center Area

A hub for healthcare and research facilities, this neighborhood offers a practical base for visitors seeking convenient access to medical institutions and related services. Comfortable vacation rentals here provide a seamless stay close to essential amenities.

View 3663+ Rentals in Medical Center Area

Best Times to Visit Fenway–Kenmore

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this destination ensures you experience its vibrant atmosphere while making the most of your stay in the area’s comfortable vacation rentals.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, the region experiences warm weather and lively events that attract many visitors seeking outdoor activities and a vibrant city atmosphere.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: around 65°F (18°C)
autumn
Fall (September to November)

Autumn brings cooler temperatures and beautiful foliage, making it an ideal time for exploring the area's cultural sights and enjoying pleasant weather before winter.

Average Temperature Daytime: around 70°F (21°C) - Nighttime: around 55°F (13°C)

Off-Season Highlights

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Winter (December to February)

Winter sees fewer visitors due to colder weather, offering a quieter experience and potential for off-season deals in the area’s cozy accommodations.

Average Temperature Daytime: around 40°F (4°C) - Nighttime: around 25°F (-4°C)
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Early Spring (March to April)

Before the full bloom of spring, this period offers lower crowds and peaceful surroundings, perfect for those seeking a more relaxed visit.

Average Temperature Daytime: around 50°F (10°C) - Nighttime: around 38°F (3°C)

Weekly Weather Forecast for Fenway–Kenmore

How to Book Your Fenway–Kenmore 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 Fenway–Kenmore

More Top-Rated Vacation Rentals in Fenway–Kenmore Area

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

  • Access to outdoor seating areas or patios where you can relax and enjoy the fresh air.
  • Green spaces or gardens nearby that allow for leisurely strolls or picnics.
  • On-site parking facilities to conveniently explore the local attractions of this destination.
  • Nearby walking or biking trails that provide scenic routes through the area.
  • Outdoor grilling stations or barbecue areas for social gatherings with friends or family.
  • Communal outdoor spaces designed for recreation or outdoor activities in the region.
  • Proximity to parks or waterfronts that offer opportunities for outdoor recreation and sightseeing.

Top Attractions Around Fenway–Kenmore

What attractions are nearby?

While staying here, you can enjoy a variety of nearby activities, including exploring local sports events, cultural attractions, and dining experiences that showcase the vibrant atmosphere of this Boston neighborhood.

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Family Activities

  • Fenway Park Tour: Experience the iconic home of baseball with a guided tour that offers a behind-the-scenes look at the historic stadium.
  • Museum of Science Boston: Engage your family with interactive exhibits and live demonstrations at this popular science museum nearby.
  • Harvard University Campus: Explore the historic grounds, beautiful architecture, and lush green spaces of this world-renowned university.
  • Public Garden and Boston Common: Enjoy leisurely strolls, playground fun, and scenic views in these central parks perfect for family outings in the area.
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Adult Activities

  • Attend a Major League Baseball Game at Fenway Park: Experience the thrill of watching our beloved Boston Red Sox in this historic ballpark, just a short distance from your vacation rental.
  • Explore the Museum of Fine Arts, Boston: Immerse yourself in world-class art collections and special exhibitions within easy reach of the vibrant neighborhoods around here.
  • Enjoy Live Performances at the House of Blues: Discover live music and nightlife options that showcase local talent and create memorable evenings close to your accommodations.
  • Stroll Through the Fenway Victory Gardens: Relax in this scenic urban garden space, perfect for leisurely walks and enjoying the outdoors during your stay in this area.

Other Places to Stay in Fenway–Kenmore, MA

Kenmore Square
Kenmore Square Vacation Rentals
Charles River Bike Path
Charles River Bike Path Vacation Rentals
House of Blues Boston
House of Blues Boston Vacation Rentals
Fenway Park
Fenway Park Vacation Rentals
New England Conservatory of Music
New England Conservatory of Music Vacation Rentals
New England Conservatory Jordan Hall
New England Conservatory Jordan Hall Vacation Rentals
Back Bay Fens
Back Bay Fens Vacation Rentals
Huntington Theatre
Huntington Theatre Vacation Rentals
Northeastern University
Northeastern University Vacation Rentals
Medical Center Area
Medical Center Area Vacation Rentals
Longwood Medical Area
Longwood Medical Area Vacation Rentals
West Fens
West Fens Vacation Rentals
More Places to Stay Near Fenway–Kenmore

Fenway–Kenmore Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Entertainment: Take advantage of the vibrant food scene and cultural venues nearby to truly immerse yourself in the area's lively atmosphere.
  • Plan Your Transportation Ahead of Time: Utilize the region’s accessible public transit options or consider renting a bike to navigate effortlessly around this popular destination.
  • Select Your Accommodation Strategically: Choose a vacation rental close to major attractions and transit hubs for maximum convenience during your stay.
  • Engage with the Local Community: Connect with neighborhood spots and events to experience authentic local life and make your trip more memorable.

Transportation Options

  • MBTA Subway:** You can easily access the region's subway system, which connects Fenway–Kenmore to downtown Boston and beyond, making travel convenient for exploring locally or venturing further.
  • Bus Services:** The area is well-served by local bus routes that provide affordable transportation options around the neighborhood and to key destinations in Boston.
  • Bike Share Programs:** Public bike-sharing services are available nearby, offering a flexible and eco-friendly way to navigate the region at your own pace.
  • Rideshare Services:** Companies like Uber and Lyft operate extensively here, providing quick and reliable door-to-door transportation tailored to your schedule.

Local Customs Options

  • Cheering at Fenway Park: Embrace the local tradition of enthusiastic baseball cheers during a game at Fenway Park, an experience that captures the spirit of the region.
  • Boston Tea Party Reenactments: Participate or observe the historical reenactments along the historic waterfront, reflecting the area's rich colonial past and revolutionary heritage.
  • Seafood Dining Etiquette: Enjoy locally loved seafood specialties such as clam chowder and lobster rolls while adhering to regional dining customs that emphasize freshness and community sharing.
  • Street Festival Celebrations: Join in on seasonal street festivals that celebrate Boston’s cultural diversity and love for music, arts, and local cuisine within the neighborhood.

Frequently Asked Questions About Fenway–Kenmore?

1. What are the top vacation rentals in Fenway–Kenmore?

There are a lot of options in Fenway–Kenmore. If you plan on staying in the Fenway–Kenmore area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Fenway–Kenmore:

2. Which vacation homes in Fenway–Kenmore are best for families?

If you are looking for a family-friendly vacation home in Fenway–Kenmore, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Fenway–Kenmore:

3. How many Rentbyowner vacation rentals are available in Fenway–Kenmore?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 291 in the Fenway–Kenmore 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 Fenway–Kenmore. 

4. What is the cancellation policy for vacation rentals in Fenway–Kenmore, Boston?

Cancellation policies vary depending on the property listing. You should review the specific policy outlined in the rental details or contact the owner directly to understand the terms and any potential fees.

5. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning charges, security deposits, or service fees are typically listed within the property details. It's recommended to read the full listing or reach out to the owner for clarification before confirming your reservation.

6. How do I find a vacation rental that meets my needs in this area?

You can filter search results based on your preferences including size, amenities, and price. Each listing provides detailed descriptions to help you choose the perfect place that suits your travel plans in this vibrant region.

7. What should I know about check-in and check-out procedures for rentals here?

Check-in and check-out times are specified in each listing. Some properties may offer flexible options, but it’s best to confirm these details with the owner during your booking process.

8. Is there a secure way to pay for my vacation rental in Boston?

Payments are processed through a secure platform provided by the booking site. Review the payment options available on the listing page or contact the owner for any specific instructions to ensure a safe transaction.

Fenway–Kenmore Top Rated Vacation Rentals

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