Holiday rentals in Bay Village

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Top-rated holiday rentals in Bay Village

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

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Top guest favourite
A living room area showcases a sectional sofa in gray, adorned with decorative pillows in varying shades. A wooden table is centrally located, accompanied by a small potted plant. Exposed brick walls add texture, while skylights infuse the space with natural light. Artwork is displayed on the walls.
Apartment in South End
4.98 out of 5 average rating, 169 reviews

*NEW* 3 BR South End Duplex with A/C in the city!

Location, location, location! This 3-BED 1-BATH penthouse duplex in a classic Boston Brownstone has the best of both worlds: a QUIET RESIDENTIAL STREET great for relaxing after a long day but STEPS FROM amazing restaurants, cafes, & bars of the South End. Looking to explore? We are a short walk from shopping on Newbury Street, history of Beacon Hill & Back Bay, or a stroll through Boston Public Garden. Want to see more? Back Bay subway Station is just around the corner! See Boston like a local!

Top guest favourite
The living area features a decorative fireplace and a 55-inch smart TV mounted above the mantel. Two large windows allow natural light to fill the space, with soft furnishings and a cozy ambiance created by tasteful decor and a chandelier.
Flat in Shawmut
4.99 out of 5 average rating, 257 reviews

Astonishing 1 Bed South End Boston's Best Location

Clean, unique, bright, inviting, 1-bedroom on the 1st floor. Newly renovated with astonishing ceilings, new tall custom windows, new appliances. The best of Boston outside your door Located half a block to Restaurant Row, where you’ll find some of the best dining in the city. Famous bakeries, coffee shops are all near, a super effortless walk to the very BEST Boston has to offer. Complimentary Keurig coffee, snacks, Netflix, movie channels, high speed internet. It doesn't get better than this!

Guest favourite
Home in Downtown
4.95 out of 5 average rating, 21 reviews

Private loft style townhouse.

Hollywood meets Boston. Make your visit to Boston one of a kind. Stay in our meticulously maintained loft-style, townhouse steps to the Boston Public Garden. This private entrance, two story townhome housed in a former film archive. A generous entrance foyer leads to main living space with soaring 16 foot ceilings, exposed brick & a wonderfully curated art collection. You will be welcomed by mirror like Terrazo floors Wall of windows & a home like no other. Enjoy the ultimate Boston experience

Guest favourite
A historic entrance features a red front door framed by white trim inside a covered porch. The space is adorned with a hanging lantern and flanked by traditional shutters on either side. A set of stairs leads up to the doorway, surrounded by exposed brick.
Flat in South End
4.84 out of 5 average rating, 243 reviews

Historic townhouse in the heart of Boston

This 1860s townhouse is located right in the heart of historic Boston. Wander onto a cobble-stoned street described by the Boston Herald as "... out of a Sherlock Holmes story." Bay Village's gas lantern-lit neighborhood was known to Paul Revere as South Cove. Edgar Allen Poe was born here. We're just steps from Back Bay, Chinatown, Theater District, South End, Boston Public Gardens, and Boston Commons. Massachusetts Room Occupancy Excise Registration Certificate Number: C0031650351

Top guest favourite
Apartment in Beacon Hill
4.96 out of 5 average rating, 124 reviews

Charming and Historic Apartment

Located in the heart of the historic Beacon Hill neighborhood, this cozy apartment is on the first two floors of a four-story brick townhouse. Tucked away on a European-style gated courtyard, the apartment is incredibly quiet and private, and only steps away from the shops, restaurants and public transportation of Charles Street and Cambridge Street. The well equipped kitchen has been recently renovated with free in unit laundry, bar, adjacent patio. Also WFH station and gas fireplace.

Guest favourite
A cozy living area is highlighted by a wooden floor and large windows, offering street views. A green armoire is positioned against a wall, complemented by a wooden dining table and chairs. A stylish lounge chair and a striped rug add character to the space.
Flat in South End
4.87 out of 5 average rating, 150 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.

Top guest favourite
A bright and cozy studio features a queen bed alongside a sleeper sofa, with an elegant coffee table positioned in front. A decorative fireplace sits against the wall, and bookshelves hold various books. Natural light floods the space through adjacent windows.
Guest suite in Downtown
4.99 out of 5 average rating, 97 reviews

Cozy studio in Bay Village near Public Garden

This newly renovated private studio is ready to welcome you! This unit has 1 queen bed and 1 sleeper sofa, a desk, a kitchenette, a full bathroom, and a washer/dryer. It is the lower level of a historic 1800s Bostonian house, recently renovated. It has its own separate entrance. Great location! Conveniently located in Bay Village next to the Boston Public Garden, the studio is close to Downtown, Theater district, Chinatown, Beacon Hill, Back Bay, and South End!

Top guest favourite
An open kitchen and dining area feature modern design elements, including an orange Smeg oven and sleek cabinetry. A large island with seating offers space for dining or food prep. Natural light is provided by skylights and a glass door leading to the deck.
Flat in Magoun Square
4.98 out of 5 average rating, 266 reviews

Hipster Basecamp | Modern • Fireplace • Parking

Welcome to Hipster Basecamp, a curated space where mid-century design meets modern comfort. Whether you're here for business or pleasure, enjoy bold touches like a double-sided fireplace, Smeg appliances, and a ceiling-mounted rain shower. Brew espresso or mix cocktails with everything at your fingertips, then head to the deck to unwind and take in the peaceful view. Admire original artwork throughout — and if a piece speaks to you, it's available for purchase.

Guest favourite
A private deck is furnished with four sleek black outdoor chairs and a small table, offering a relaxing space. The view overlooks historic brick buildings, with greenery visible in the background, adding to the serene atmosphere.
Flat in Chinatown
4.83 out of 5 average rating, 500 reviews

Special Winter Rates! Private Deck Parking 4 Rent

We're excited to hosts lucky guests with tickets to FIFA at Gillette in June! Under a mile from the apartment to South Station where you can take the special commuter rail train directly to the stadium! Exquisitely decorated, one-bedroom apartment in the historic downtown pocket neighborhood, Bay Village. Steps to Theatre District, 5-minute walk to subway, 10-minute walk to Whole Foods. Three miles from the airport. Parking available for rent, $30 per night.

Top guest favourite
A living area features a contemporary black sofa and two matching armchairs arranged around a round glass coffee table, all placed on a vibrant blue rug. A large artwork hangs on the wall, and a window allows natural light to enter the space.
Apartment in South End
4.99 out of 5 average rating, 107 reviews

1 Bedroom Apartment in Boston/South End

One bedroom condo on parlor level on quiet South End street. Convenient to all the restaurants, Back Bay, Financial District, Downtown. There are stairs leading to the building. Full size bed, full-size tub with shower in bathroom. Wi-Fi. Listing is for the full apartment. Two guests only. No one under 18. No visitors or parties. There is no street or designated parking. Best for one or two people visiting and enjoying the city.

Guest favourite
A bright living area is highlighted by a circular dining table surrounded by four chairs. A large round mirror above a white fireplace reflects the light. Warm wooden floors contrast with the cream walls, accentuated by subtle decor elements and natural light from nearby windows.
Apartment in Bay Village
4.88 out of 5 average rating, 144 reviews

Condo in downtown Boston

Quintessential Boston Brownstone. Private patio, 2 bedroom, 1.5 bath. Welcome to Bay Village! The most central location in Boston with a safe, residential feel. This condo is perfectly well kept, newly furnished, & comfortable with Central Air. We have a desk set-up for WFH, and kitchenware to cook a fabulous meal. Take a few steps out of the condo and enjoy all the Boston has to offer! STR544848

Top guest favourite
A pair of large, double doors with a rich, textured surface stands prominently in the background. The doors are flanked by warm, wooden floors and a light-colored sofa adorned with decorative pillows. A vibrant area rug adds color to the setting.
Apartment in Downtown
4.97 out of 5 average rating, 186 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.

Popular amenities for Bay Village holiday rentals

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Quick stats about holiday rentals in Bay Village

  • Total holiday rentals

    Explore 260 holiday rentals in Bay Village

  • Verified guest reviews

    Over 10,830 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 140 rentals that welcome pets

  • Rentals with dedicated workspaces

    190 properties have a dedicated workspace

  • Wifi availability

    250 of Bay Village holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Bay Village rentals

  • 4.5 Average rating

    Bay Village stays receive an average rating of 4.5 out of 5 from guests

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