Discover Your Perfect Cleveland Circle Vacation Homes

Cleveland Circle Luxury Rentals

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Cleveland Circle Pet Friendly Vacation Rentals

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Cleveland Circle Large Vacation Homes

9.3 (91 Reviews)
Bed & Breakfast
Natalie House
  • Air Conditioner
  • Parking
  • TV
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6.5 (245 Reviews)
Bed & Breakfast
Beacon Inn 1750
  • Air Conditioner
  • Parking
  • Security/Safety
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Why Choose Rent By Owner for your Cleveland Circle 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 Cleveland Circle Vacation Rentals

Where are the best neighborhoods to stay in Cleveland Circle?

When considering where to stay in Boston, Cleveland Circle offers a welcoming neighborhood that combines convenient access to the city with a relaxed community atmosphere. Located in the southwestern part of Boston, this neighborhood is ideal if you're looking to enjoy a peaceful retreat while still being close to vibrant city attractions. With easy transportation links and nearby parks, Cleveland Circle provides the perfect setting for a comfortable and enjoyable stay. Whether you're exploring local shops or simply relaxing at your vacation rental, you'll find this area to be both accessible and inviting for your Boston experience.

Allston

Known for its vibrant arts scene and diverse community, this neighborhood offers convenient access to Boston’s cultural hubs and nightlife. Staying here places you in a lively area perfect for exploring local music venues, cafes, and eclectic dining options.

View 53+ Rentals in Allston

Brighton

This region blends residential charm with easy transit connections, making it an ideal choice for visitors seeking comfort combined with accessibility. Its friendly atmosphere and proximity to parks provide a peaceful retreat while still keeping you close to the city’s attractions.

View 92+ Rentals in Brighton

St. Elizabeth's

Offering a quiet, community-oriented environment, this neighborhood is well-suited for those who prefer a tranquil stay within reach of Boston’s bustling city life. It’s an excellent base for exploring the region while enjoying a more relaxed setting.

View 47+ Rentals in St. Elizabeth's

Commonwealth

Rich in history and local character, this area provides a charming backdrop for your visit, with easy access to Boston’s central districts. Choosing accommodations here ensures a comfortable and authentic experience in the region’s vibrant neighborhoods.

View 30+ Rentals in Commonwealth

Aspinwall Hill

Perched atop a scenic hill, this neighborhood offers stunning views along with a peaceful residential ambiance. It’s a perfect spot for travelers wanting a quiet retreat that’s still close to Boston’s main attractions and amenities.

View 1869+ Rentals in Aspinwall Hill

Woodland Heath

Surrounded by lush greenery and natural beauty, this area is ideal for nature lovers seeking a serene environment. It provides a picturesque setting for your stay while remaining accessible to the city’s cultural and historical sites.

View 820+ Rentals in Woodland Heath

Oak Square

A hub of community activity and convenience, this neighborhood offers easy transit options and local amenities suited for exploring Boston and beyond. It’s a practical choice for travelers looking for both comfort and connectivity during their visit.

View 1008+ Rentals in Oak Square

Best Times to Visit Cleveland Circle

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can significantly enhance your experience, allowing you to enjoy the region's unique charm at its best and ensuring a smooth booking process for your ideal vacation rentals.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During this period, the area experiences pleasant weather ideal for outdoor exploration and enjoying local amenities. Expect higher demand for vacation rentals as visitors flock here to enjoy the region's scenic beauty.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September to October)

This season offers comfortable temperatures and vibrant fall foliage, making it a popular time to visit. The increased activity boosts the availability of premium vacation rentals for your stay here.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Mid Winter (January to February)

During these colder months, fewer travelers visit, providing you with more affordable options if you prefer a quieter experience in this destination.

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

As the region transitions into winter, visitor numbers decrease, making it an advantageous time to find excellent deals on vacation rentals while enjoying fewer crowds here.

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

Weekly Weather Forecast for Cleveland Circle

How to Book Your Cleveland Circle 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 Cleveland Circle

More Top-Rated Vacation Rentals in Cleveland Circle 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

  • Enjoy a private outdoor seating area or patio to unwind after exploring the surrounding neighborhood.
  • Take advantage of on-site gardens or landscaped courtyards that showcase the region’s natural beauty.
  • Make use of outdoor grilling facilities for a convenient barbecue in the outdoor space.
  • Spend time relaxing on shared or private balconies with views of the local scenery.
  • Benefit from nearby parks and green spaces perfect for outdoor activities or picnics.
  • Look for outdoor swimming pools available at some properties for a refreshing dip during your stay.
  • Utilize outdoor recreational amenities such as tennis courts or walking trails in the vicinity.

Top Attractions Around Cleveland Circle

What attractions are nearby?

Within this vibrant area, you can indulge in outdoor activities along scenic trails, enjoy the local parks, or explore nearby cafes and shops, making your stay in Cleveland Circle an ideal base for discovering Boston’s many attractions.

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Family Activities

  • Boston College Campus Tour: Explore the picturesque grounds of one of the region’s renowned universities, offering family-friendly walking tours and scenic spots for a relaxing outing.
  • The Riverway Park: Enjoy outdoor activities like picnicking, walking, or biking along this scenic park that runs adjacent to the Charles River, perfect for a day with the children.
  • Cleveland Circle Greenway: Take a family stroll or bike ride along this peaceful greenway, which provides beautiful views and easy access to nearby recreational areas.
  • Nearby Fresh Pond Reservation: Visit this natural haven for wildlife observation, kayaking, or family-friendly trails that make for an engaging outdoor experience here.
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Adult Activities

  • Fenway Park Tour: Experience the thrill of a guided tour at this iconic baseball stadium, immersing yourself in Boston's rich sports history.
  • The Emerald Necklace Parks: Enjoy a leisurely stroll or bike ride through these historic parklands that offer scenic views and tranquil outdoor spaces nearby.
  • Cleveland Circle Dining: Indulge in a variety of local eateries and cafes perfect for relaxing after a day exploring the area's attractions.
  • Boston University Campus Visit: Explore the vibrant campus atmosphere and admire the historic architecture within this renowned university community.

Other Places to Stay in Cleveland Circle, MA

St. Elizabeth's Medical Center
St. Elizabeth's Medical Center Vacation Rentals
SMG Brighton Primary Care
SMG Brighton Primary Care Vacation Rentals
Chestnut Hill Reservoir
Chestnut Hill Reservoir Vacation Rentals
Brighton
Brighton Vacation Rentals
St. Elizabeth's
St. Elizabeth's Vacation Rentals
Commonwealth
Commonwealth Vacation Rentals
More Places to Stay Near Cleveland Circle

Cleveland Circle 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 visiting local restaurants to enjoy authentic flavors unique to the region.
  • Utilize Public Transportation: Maximize your stay by using public transit options, such as buses and trains, for convenient access to Boston's top attractions.
  • Discover Hidden Gems: Spend time exploring lesser-known parks and scenic spots around here to experience the area's natural beauty beyond popular tourist sites.
  • Plan Your Day in Advance: Organize your itinerary ahead of time to make the most of your visit and ensure you don’t miss out on the area's must-see destinations.

Transportation Options

  • Green Line Trolley Service: This light rail option provides quick, reliable transportation directly into downtown Boston and surrounding neighborhoods from Cleveland Circle.
  • Bus Routes: Several MBTA bus lines serve the area, offering convenient connections to key destinations across the city and beyond for your stay here.
  • Bike Sharing Programs: Bike-sharing services are widely available, allowing you to explore the region at your own pace along designated bike lanes and scenic routes.
  • Car Rentals and Rideshare Services: Renting a car or using rideshare apps offers flexibility for exploring the broader Boston area and nearby attractions during your vacation here.

Local Customs Options

  • Boston University Traditions: Local students and residents honor the university’s history through various annual events that symbolize academic excellence in this college town.
  • Community Breakfasts and Festivals: Participating in neighborhood gatherings and seasonal festivals reflects the area's friendly and welcoming spirit.
  • Sports Fandom: Cheering for local teams at game day celebrations highlights the region's passionate sports culture.
  • Historical Commemorations: Observing key historical anniversaries and heritage days demonstrates respect for the area's rich past.

Frequently Asked Questions About Cleveland Circle?

1. What are the top vacation rentals in Cleveland Circle?

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

2. How many vacation rentals have private pools in Cleveland Circle?

There are 1 vacation rentals with private pools near Cleveland Circle. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Cleveland Circle are best for families?

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

4. How many Rentbyowner vacation rentals are available in Cleveland Circle?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 127 in the Cleveland Circle 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 Cleveland Circle. 

5. What is the cancellation policy for vacation rentals in Cleveland Circle, Boston?

Cancellation policies vary by property, so you should review the specific listing details or contact the property owner directly to understand the terms and any potential fees involved.

6. How do I communicate with the property owner before booking a vacation rental in the area?

You can reach out to the property owner through the messaging feature on the booking platform to ask questions and confirm details before finalizing your reservation.

7. Are there any house rules I should be aware of when staying in a vacation rental here?

Yes, each property has its own set of house rules, which are detailed on the listing. Make sure to read these carefully to ensure a smooth stay.

8. What amenities are typically included in vacation rentals in this part of Boston?

Amenities vary but often include essentials like Wi-Fi, kitchen facilities, and parking. Review the specific listing for a comprehensive list of what’s offered.

9. Is there a minimum stay requirement for booking vacation rentals in Cleveland Circle?

Minimum stay requirements depend on the property and the season; details are available on each listing or can be clarified by contacting the owner directly.

Cleveland Circle Top Rated Vacation Rentals

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