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Holiday rentals in Downtown

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Top-rated holiday rentals in Downtown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The foyer entrance showcases a historical charm, featuring original ornate wallpaper and hardwood floors. A grand staircase is visible in the background, with modern light fixtures illuminating the space. A plush green chair adds a touch of elegance to this welcoming area.
Flat in Boston
4.94 out of 5 average rating, 49 reviews

Charlesgate Suites: Renovated & Ready To Host You!

Welcome to Charlesgate Suites! We eagerly await the opportunity to host you in our recently renovated hotel, which has undergone a stunning transformation from a traditional B&B into a trendy & dynamic space. With no front desk & a seamless self check-in, we ensure a hassle-free arrival experience. Each of our exquisitely designed rooms showcases the perfect balance of modern aesthetics & comfort, featuring stylish West Elm furnishings. Please note this room is on the 2nd floor with no elevator.

Flat in South End
4.69 out of 5 average rating, 190 reviews

Stylish Downtown Studio in the SouthEnd, C.Ave# 41

The unit is stylishly designed for comfort, value and convenience. Centrally located on the line Boston’s Back Bay and South End. Quaint and chic are just 2 words to describe Boston’s South End neighborhood. In the past few years, the South End has grown to be one of Boston’s hottest neighborhoods built with families and young professionals in mind. Loaded with restaurants (some of the best in the city), art galleries, and boasting a modern industrial vibe, the South End is an ideal destination.

Top guest favourite
Flat in Huron Village
5 out of 5 average rating, 24 reviews

Apartment in Cambridge

This is a charming 2-bedroom in lovely tree-lined Huron Village. Newly renovated, the space offers a full kitchen and bathroom, tasteful furnishings, and in-wall air conditioning. Enjoy being just moments from the delightful shops, cafés, and bakeries of Huron Village, with Fresh Pond trails nearby for outdoor activities and bustling Harvard Square just a 20-min walk away. On the 2nd of 3 floors, the place gets plenty of natural light, with responsive hosts downstairs and on-site parking.

Guest favourite
Flat in Brighton
4.96 out of 5 average rating, 144 reviews

The Murthy : Bright • Spotless • W/D

Enjoy Boston in this elegant suite for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

Guest favourite
Flat in South End
4.86 out of 5 average rating, 154 reviews

The Upton - The Upton Boston, South End

See more photos at our IG @theuptonboston The Upton was designed to be the ideal home base. Staying here means you are next to restaurants, shopping, site-seeing, & visiting family in the South End. Ideal for business travel or tourism. Our guests choose us for our historic charm and perfect location. The Upton features 2 dining (or work) spaces with expansive Victorian windows giving way to views of Tremont Street & a leafy, calm side street. We look forward to hosting you.

Guest favourite
The living area features a spacious sofa and two accent chairs, complemented by a decorative rug and a round coffee table. Large windows provide ample natural light, with city views visible through the glass. Vintage-style moldings decorate the high ceilings.
Flat in South End
4.9 out of 5 average rating, 68 reviews

The Chester: Penthouse One Bedroom

Discover The Chester, A Boutique Stay in the heart of the South End. Designed to accommodate up to 4 guests, this space features a king bed, a queen pull-out, and a fully equipped kitchen. Enjoy city views, classic Boston Brownstone original crown moldings, smart TVs, and a sleek, modern tiled shower. Expertly decorated with a mix of contemporary and antique furnishings, this urban retreat offers comfort and style at the heart of the vibrant city.

Guest favourite
Apartment in Boston
5 out of 5 average rating, 13 reviews

806B City Views Brand New Studio Downtown District

✨BRAND NEW✨ 1 King-Bed Luxury Studio with private upgraded bathroom & fully-stocked kitchen, located right at Boston Commons and Downtown! NO SHARING OF RESTROOMS OR KITCHEN! *No children under 12. 📍 Centrally located to be able to walk anywhere needed and 200-400 ft. to multiple T stops 🚊. Perfect for traveling professionals, mid-term stays and more! ALL UTILITIES INCLUDED. 451 sq. feet. 8th floor. Elevator access, no stairs.

Flat in Downtown
4.79 out of 5 average rating, 214 reviews

Bay Village Charm | 99 WalkScore | Short/Long Stay


This 1bed, 1bath apartment has laundry in the basement of the building and located on a quiet street just 2 minutes from the Boston Public Gardens.  Large windows let in lots of light! Fully stocked kitchen has everything you'd need to cook a basic meal.  The unit is accessible by self-check-in via our smart lock system. 
 Its a 10 min trip to Mass General Hospital by car or Public Transportation and the walk is about

Top guest favourite
Apartment in Downtown
4.97 out of 5 average rating, 189 reviews

Downtown Loft Boston - Close to everything

Spacious loft in Downtown Boston, Historic District, with high ceilings, large windows, original wooden floors, private bedroom area-queen bed, also sofa in living room can become a pull-out double size bed. The bathroom is with shower and tub, a complete kitchen, and laundry room. The unit also offers the highest speed available in the area -1 gig internet access and 55" smart TV.

Guest favourite
Flat in Beacon Hill
4.92 out of 5 average rating, 12 reviews

The Beacon Hill Residence

Enjoy full privacy in this entire apartment—no shared spaces. Welcome to 40 Hancock Street, a charming brownstone in Beacon Hill. Enjoy easy access to Boston Common, the Charles River, and the city’s best restaurants, shops, and historic sights—all just minutes from your door. With comfort, style, and unbeatable location, this is the ideal place to stay for your Boston adventure.

Guest favourite
Flat in Boston
4.92 out of 5 average rating, 12 reviews

(Mlb4) NEW! Studio, Close to MGH, Boston Commons

📍 Stay in the heart of Back Bay, just steps from Newbury Street, the Prudential Center, and Copley Square. This inviting space is close to Boston’s top hospitals—Mass General, Brigham and Women’s, Boston Children’s—prestigious universities like 🎓 Harvard, MIT, BU, and Northeastern, and iconic landmarks such as Boston Common, the Freedom Trail, and the Museum of Fine Arts.

Top guest favourite
An open-concept living area features polished concrete floors and high ceilings. A spacious white sectional couch adorned with accent pillows faces a glass coffee table. The area is filled with natural light streaming through large windows, while a cozy sleeping space with a queen bed is visible in the background.
Loft in Downtown
4.97 out of 5 average rating, 381 reviews

Bright & Spacious Loft Steps to the Freedom Trail

Welcome to our light-filled, open-concept loft in the heart of downtown, just a 4 minute walk to Boston Common and the start of the Freedom Trail. Close to the Public Garden, Theater District, Beacon Hill, North End, Back Bay, Harborwalk and more! Recently updated with a brand new memory foam mattress, new Casper pillows, and a new Samsung smart washer and dryer.

Popular amenities for Downtown holiday rentals

When is the best time to visit Downtown?

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Quick stats about holiday rentals in Downtown

  • Total holiday rentals

    Explore 1,010 holiday rentals in Downtown

  • Verified guest reviews

    Over 55,550 verified reviews to help you choose

  • Family-friendly holiday rentals

    290 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 370 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    610 properties have a dedicated workspace

  • Wifi availability

    1,000 of Downtown holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Downtown rentals

  • 4.7 Average rating

    Downtown stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Downtown’s top spots include Boston Common, New England Aquarium and Boston Public Garden

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Suffolk County
  5. Boston
  6. Downtown