Oak Square holiday lettings
We found 91 holiday rentals — enter your dates for availability
Discover a selection of 9 apartments and other holiday rentals in Oak Square that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.
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Find the best place to stay - Oak Square
The Sunset Room at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
The Sanctuary at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
The Pistachio Room at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
The King's Room at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
The Tower Room at TPH - Boston
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
The Harvard Room conveniently near BC & Harvard
Sleeps 2 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
38 reviews(38 reviews)
Top rated rentals - Oak Square
Excellent as always
1010 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
We stay in this lovely apartment when we are visiting our son at college. Erin and Gerry are perfect hosts, very communicative and helpful. The area is beautiful and quiet. I can't fault it. We'll be back!
Christine B.
Stayed Feb 2025
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental in Oak Square?
In Oak Square, apartments are a popular choice for holiday rentals, with several available throughout the area. These apartments typically feature modern amenities such as fully equipped kitchens, comfortable living areas, and access to communal facilities. Many also include outdoor spaces like balconies or patios, great for enjoying the fresh air after a day of exploring the local sights.
How much does it cost to rent a holiday home in Oak Square?
Prices for holiday 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 holiday 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 rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, and onsite parking for added convenience. Many properties also feature coffee and tea makers, great for enjoying a warm beverage in the morning. Outdoor spaces are common as well, with patios or decks available for relaxation and socialising, making the most of the pleasant surroundings.
Are there any family house rentals in Oak Square?
In Oak Square, Massachusetts, there are several family-friendly house rentals available, making it a great choice for those travelling with children. The area features a range of homes that often include spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can play. Many properties also come with modern conveniences such as Wi-Fi and air conditioning, ensuring a comfortable stay for all guests.
Can I rent a holiday home with a pool or hot tub in Oak Square?
In Oak Square, Massachusetts, there are several holiday homes available for rent that offer pools and hot tubs, making it a delightful choice for travellers seeking relaxation. This charming neighbourhood, part of Brighton, is known for its family-friendly atmosphere and proximity to local parks. Many of the rentals feature modern amenities, including private hot tubs, outdoor spaces for barbecues, and fully equipped kitchens for those who enjoy cooking. Guests can also expect comfortable living areas and, in some cases, access to shared pools, which enhance the overall experience.
Are there any Oak Square holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Oak Square with parking available—perfect for families or travellers 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.
Are there pet-friendly holiday rentals in Oak Square?
In Oak Square, Massachusetts, there are several pet-friendly holiday rentals available for those looking to enjoy a stay with their furry companions. Many of these accommodations come equipped with amenities such as fully stocked kitchens, comfortable living areas, and outdoor spaces where pets can roam freely. The neighbourhood itself is known for its charming residential vibe, making it an inviting place for pet owners.
Can I find long-stay holiday rentals in Oak Square?
A long-stay holiday rental in Oak Square is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Oak Square for a holiday rental?
The best time to visit Oak Square for a holiday rental is during the peak season from May to July, when the area comes alive with vibrant activities and pleasant weather. This period is especially popular among families and groups seeking to enjoy outdoor adventures, local festivals, and the charm of the surrounding neighbourhoods. With temperatures in the mid to high 20s Celsius, it's a superb time for leisurely strolls, picnics in the parks, or exploring the local shops and restaurants.
July stands out as the most popular month, bustling with events and a lively atmosphere that creates an inviting environment for all types of travellers. You'll find plenty of opportunities to engage with the community, enjoy outdoor concerts, and take part in local celebrations that showcase the rich culture of the area.
If you're looking for a more budget-friendly option, consider visiting in December. While this is the low season, it offers a unique charm with holiday decorations, festive events, and a more relaxed pace. You can take advantage of lower rental rates while still enjoying the warmth of the local hospitality.
Are there any remote work holiday rentals in Oak Square?
In Oak Square, Massachusetts, there are several holiday rentals suitable for remote work. Many of these properties come equipped with amenities that cater to professionals, including reliable Wi-Fi, dedicated desk spaces, and ergonomic chairs. Some may even feature office setups complete with computer monitors, making it easy for guests to maintain productivity during their stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Oak Square holiday rental?
Book your Oak Square holiday 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 holiday 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?
In Oak Square, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's local charm and community spirit. The Oak Square YMCA offers numerous recreational activities and fitness classes for those looking to stay active. Nearby, the historic Brighton Allston area showcases lovely parks and green spaces, such as the scenic Brighton Common, ideal for leisurely strolls or picnics.
Can I change or cancel my Oak Square home rental booking on Vrbo?
To find Oak Square holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Oak Square holiday 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.