Oak Square vacation rentals

We found 95 vacation rentals — enter your dates for availability

Discover a selection of 8 apartments and other vacation rentals in Oak Square that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the best amenities for spending time at your vacation home, such as WiFi and cable TV. What you'll find is a rental to meet everyone's needs, including places that are non-smoking or accessible.

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Find out more about Oak Square

Why visit Oak Square

  • Family-Friendly Atmosphere: Oak Square is perfect for family vacations with a welcoming vibe and numerous activities suitable for all ages.
  • Cultural Exploration: The area offers rich urban history and local culture, making it ideal for those seeking cultural enrichment.
  • Charming Neighborhood: Oak Square Brighton features friendly locals and a vibrant atmosphere, enhancing your travel experience.
  • Proximity to Attractions: Enjoy nearby parks and local eateries that enrich your stay without straying far from the neighborhood.
  • Diverse Accommodations: Choose from cozy apartments, spacious homes, or modern condos, catering to various group sizes and preferences.

Popular types of accommodation around Oak Square

Discover the charm of Oak Square with our diverse selection of vacation rentals. Whether you prefer cozy apartments, spacious houses, or modern condos, we have something for every traveler. Our Oak Square apartments and rentals are perfect for families or groups looking for comfort and convenience. Explore the options for bedroom apartments in this vibrant Boston neighborhood, and find the ideal home away from home for your next getaway.

  • Apartments: The top choice for visitors in Oak Square, offering spacious living and amenities for a comfortable stay.
  • Houses: A great option for families or groups seeking privacy and a home-like atmosphere.
  • Condos: Stylish and convenient, condos provide a blend of comfort and modern living for travelers.
  • House Boats: Unique and charming, houseboats offer a memorable experience on the water in Oak Square.
  • Cottages: Cozy and quaint, cottages are perfect for those wanting a peaceful retreat.**

Top attractions near Oak Square

Oak Square in Boston is a fantastic destination for culture, city, and family vacations. Visitors can explore notable attractions such as urban parks, medical centers, and local streets. This vibrant area offers a blend of experiences that cater to travelers seeking cultural enrichment and family-friendly activities. Don't miss the charm of Oak Square Brighton, which adds to the appeal of your visit.

  • Fenway Park: A historic sports stadium, Fenway Park offers a vibrant atmosphere filled with rich baseball culture. Experience the excitement of a game and immerse yourself in the history of America's pastime.
  • Boston Common: As the oldest public park in the U.S., Boston Common features beautiful landscapes perfect for family outings. Enjoy leisurely strolls, picnics, and various outdoor activities amidst the city’s natural beauty.
  • Copley Square: This modern square is a hub of city life, showcasing stunning architecture and bustling energy. Visit local shops, dine at nearby restaurants, and enjoy cultural events in this vibrant urban space.

Things to do recommended for couples

For a romantic getaway near Oak Square, consider the luxurious Country Club of Billerica, 15 miles away, or the elegant Tewksbury Country Club, 17 miles away. Both offer a perfect setting for couples seeking a memorable experience filled with charm and sophistication.

Things to do recommended for families

Families visiting Oak Square can enjoy a fun-filled day at the nearby Boston Children's Museum, packed with interactive exhibits, and explore the beautiful parks and playgrounds perfect for kids to play and enjoy the outdoors.

Things to do recommended for groups

Explore the vibrant local culture at the Oak Square YMCA or enjoy a group game at the nearby Brighton Common. For a taste of history, visit the historic churches in the area or take a short ride to the Boston Museum of Fine Arts for an enriching afternoon.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Oak Square

If you're traveling with a group, family, or pets, or planning an extended stay, be sure to use the appropriate filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Oak Square with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these options and more on Vrbo.
  • Traveling to Oak Square with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Oak Square: For many families, a trip isn't truly complete without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Oak Square: If you're searching for vacation rentals that offer special rates for extended stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also want to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Oak Square

Oak Square is a charming neighborhood in Boston, ideal for family vacations and cultural explorations. Just a stone's throw from downtown Boston, visitors can enjoy friendly neighborhoods and affordable housing. The area boasts a vibrant atmosphere filled with urban history and welcoming locals. Nearby attractions, including parks and local eateries, enhance the travel experience, making Oak Square a perfect base for discovering the rich culture and excitement of Boston.

  • Boston: Boston is a vibrant metropolis rich in history and culture, making it a must-visit destination for tourists. As the birthplace of the American Revolution, this city offers a plethora of historic sites and landmarks, such as the Freedom Trail, the Boston Tea Party Ships and Museum, and Fenway Park. Travelers can enjoy diverse activities, from attending music concerts to shopping at local boutiques in areas like Newbury Street. Boston's educational institutions, including Harvard and MIT, add to its allure, making it a hub for families, culture enthusiasts, and business travelers alike.
  • Cambridge: Located just 3 miles from Oak Square, Cambridge is renowned for its prestigious universities and vibrant arts scene. Visitors can explore the historic campuses of Harvard University and the Massachusetts Institute of Technology (MIT), or indulge in retail therapy at the eclectic shops and restaurants along Harvard Square. Cambridge offers a unique blend of scholarly charm and urban energy, with attractions such as the Harvard Art Museums and the Cambridge Science Festival. This city is perfect for family outings, cultural experiences, and business meetings, providing a stimulating environment for all.
  • Brighton: Brighton is a charming neighborhood located 0.7 miles from Oak Square, known for its community feel and accessibility to urban amenities. This area features a mix of modern and historic college universities, making it popular among students and families. Visitors can enjoy a variety of shopping options at local malls and centers, as well as explore parks and recreational spaces. Brighton's proximity to Boston allows for easy access to the city's attractions while offering a quieter atmosphere, making it an ideal spot for those looking to experience both the hustle of the city and the comfort of a residential neighborhood.

Best time to go to Oak Square

If you're planning a trip to Oak Square, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and October, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.0°F (-1.1°C)Light RainMostly SunnyModerately LowSlightly Low
February31.5°F (-0.3°C)Light RainMostly CloudyModerately LowSlightly Low
March37.9°F (3.3°C)Light RainMostly SunnyAverageSlightly Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnyModerately HighSlightly High
July73.6°F (23.1°C)Light RainMostly SunnyModerately HighSlightly High
August72.7°F (22.6°C)Light RainMostly SunnyAverageAverage
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October55.6°F (13.1°C)Light RainMostly SunnyModerately HighSlightly High
November44.4°F (6.9°C)Light RainMostly SunnyAverageAverage
December36.3°F (2.4°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can change significantly. Also, opting for a longer stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's innovative Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily find the properties you've saved and booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Oak Square?
In Oak Square, apartments are among the most popular types of vacation rentals, with several options available throughout the area. These apartments typically feature modern amenities such as fully equipped kitchens, comfortable living spaces, and often include laundry facilities for added convenience. Many are located in vibrant neighborhoods close to local parks and dining options, providing easy access to the community's attractions.

Additionally, vacation houses and condos also have a presence in Oak Square, offering travelers more space and the comforts of home. These properties often include multiple bedrooms, private outdoor spaces, and amenities like BBQ grills, making them ideal for families or groups.
Are there any beach house rentals in Oak Square?
In Oak Square, there are beach house rentals available, providing a charming option for travelers looking to enjoy a coastal getaway. These rentals typically feature amenities such as multiple bedrooms, fully equipped kitchens, and spacious living areas, ideal for families or groups. Many properties also include outdoor spaces like decks or patios, great for relaxing after a day at the beach. Find your rental near the beach in Oak Square.
How much does it cost to rent a vacation home in Oak Square?
Prices for vacation rentals in Oak Square 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Oak Square to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Oak Square vacation house rentals?
You can find great discounts on house rentals in Oak Square on Vrbo, 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.
What are popular rental amenities in Oak Square?
In Oak Square, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals conveniently. Onsite parking is also a common feature, making it easy for guests with vehicles to access the area. Many rentals offer a coffee or tea maker for those who enjoy a warm beverage, and outdoor spaces such as decks or patios provide a superb spot for relaxation. Additionally, rentals often come with a desk, suiting guests who may need to work or study during their stay.
Can I find family house rentals in Oak Square?
In Oak Square, Massachusetts, there are some available family-friendly house rentals that cater well to groups. This charming neighborhood offers a variety of properties, many of which feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for children to enjoy.

Visitors will appreciate the convenience of nearby parks, where families can enjoy recreational activities, and the vibrant local community that often hosts events and activities. Additionally, the proximity to attractions in Boston, such as the Boston Museum of Fine Arts and the historic Fenway Park, enhances the appeal of staying in this area.
Are there any Oak Square vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Oak Square with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
Can I book pet-friendly vacation rentals in Oak Square?
In Oak Square, Massachusetts, there are several pet-friendly vacation rentals available, making it a great option for travelers looking to bring their furry friends along. The area features a mix of accommodations, including cozy apartments and spacious homes that often come equipped with amenities such as full kitchens, laundry facilities, and outdoor spaces where pets can enjoy some fresh air.

Oak Square is conveniently located near parks and green spaces, providing ample opportunities for pet owners to take their dogs for walks or play. The nearby Brighton Common and the larger Chestnut Hill Reservation offer lovely trails and open areas, superb for enjoying nature with pets. Additionally, the neighborhood has a variety of pet-friendly cafes and shops, ensuring that both you and your pet can have a pleasant stay.
Can I find long-stay vacation rentals in Oak Square?
A long-stay vacation rental in Oak Square is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Oak Square for a vacation rental?
The best time to visit Oak Square for a vacation rental is during the peak season, which spans from May to July. This period is particularly vibrant, attracting travelers who are eager to enjoy the warm weather and a variety of festivities in the area. With temperatures typically ranging from the mid-60s to the high 80s Fahrenheit, it's an ideal time for outdoor activities, exploring local parks, and indulging in the community's rich cultural scene.

July stands out as the most popular month, where you can immerse yourself in the lively option created by summer events and local gatherings. Families and adventure seekers alike flock to the area, making it a great time to connect with fellow travelers and enjoy the abundant activities available, from outdoor concerts to seasonal fairs.

If you're looking for a more budget-friendly experience, consider visiting in December. While this month may be quieter, it offers a unique charm with holiday decorations and community events that can provide a cozy and festive atmosphere. You'll also find more availability in vacation rentals, allowing you to enjoy a more personalized experience.
Are there any remote work vacation rentals in Oak Square?
In Oak Square, Massachusetts, there are around 10 vacation rentals suitable for remote work. This vibrant neighborhood offers a mix of residential charm and urban convenience, making it an appealing choice for those looking to combine work and leisure. Many of the available rentals feature dedicated workspaces, including desks and comfortable chairs, ensuring a productive environment.

Additionally, travelers can expect amenities such as free Wi-Fi, which is essential for remote work, along with cozy living areas that provide a comfortable atmosphere for downtime. The area boasts easy access to local cafes and parks, superb for taking breaks or enjoying outdoor activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Oak Square vacation rental?
Book your Oak Square vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Oak Square, Massachusetts, United States of America?
In Oak Square, Massachusetts, visitors can explore a variety of attractions that reflect the local culture and community spirit. The area is known for its charming residential streets and local parks, such as the nearby Brighton Common, which offers green spaces for picnicking and leisure activities.

Close by, the historic St. Elizabeth's Medical Center can be noted for its significant presence in the neighborhood. The area is also well-connected to the vibrant Brighton neighborhood, where travelers can find a range of dining options, cafes, and shops that showcase the local cuisine and atmosphere.

For those interested in outdoor activities, the nearby Charles River Reservation provides scenic walking and biking paths along the river, making it a great spot for leisurely strolls or more active pursuits.
Can I change or cancel my Oak Square home rental booking on Vrbo?
To find Oak Square vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Oak Square vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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