Holiday houses 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
Apartment in South End
4.99 out of 5 average rating, 260 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 Back Bay
4.94 out of 5 average rating, 35 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 modern kitchen area is visible, featuring sleek cabinetry and stainless steel appliances. A breakfast bar with two red stools offers a cozy dining option. Gleaming hardwood floors extend into the adjoining living space, illuminated by natural light from nearby windows.
Apartment in South End
4.97 out of 5 average rating, 304 reviews

S End/B Bay border! Copley Location- Perfect 1 Br

Elegant, Spotless and Perfectly Located on the South End/Back Bay border! Best Location in Boston! Picturesque & serene Lawrence Street. Pristine, Sleek & beautifully furnished 1 bdrm 1 bath home. 1 block to Copley Sq/Pru, Back Bay station. 3 blocks to Newbury St. Gleaming hardwood floors, full kitchen with SS appliances, and granite counters. Large bedroom with en-suite bathroom. Private Washer & Dryer. Brick paved, tree-lined, quiet street in the historic South End district. Walk score 98!

Guest favourite
The image showcases the exterior of a modern transportation hub, characterized by a striking arched wooden structure. The entrance features large glass doors, and colorful banners hang above. Pedestrians and vehicles are visible on the busy street, under clear blue skies.
Apartment in South End
4.86 out of 5 average rating, 154 reviews

The Upton - The Upton Boston, South End

As featured in the June 4th Conde Nast online - 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.

Superhost
A modern kitchen layout features a wooden dining table at the center and sleek cabinetry adorned with simple hardware. Sunlight illuminates various houseplants placed on the windowsill, with a patterned backsplash adding visual interest. A pendant light hangs above the table, enhancing the space.
Condo in Somerville
4.97 out of 5 average rating, 59 reviews

2 BR apt near subway w/ parking

Colorful, modern, and convenient! This is my primary residence, and I usually share the space with guests while I'm in town. But the entire place is for rent while I'm away in July/August. The apartment has 2 bedrooms and 1.5 bathrooms. You may park up to 2 cars in the driveway next to the house. The Gilman Square subway station is only a 4-minute walk away. Only a few quick stops to Boston! Coffee, tea, and basic cooking items (sugar, oil, spices etc.) will be provided for you.

Top Guest favourite
Condo in South End
4.99 out of 5 average rating, 112 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. Best for one or two people visiting and enjoying the city. No laundry facilities for use in the building. Window units for AC in summer.

Top 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.
Apartment in Downtown
4.84 out of 5 average rating, 516 reviews

Dream Location! Private Deck, Parking for 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
Condo in Charlestown
4.98 out of 5 average rating, 151 reviews

Large 1+bed in historic Charlestown, Boston!

Large 1 BR condo. This is a brick 3 story home & the rental condo is on the 1st floor only. KING bed, work desk area, living room w/queen pull out bed, fully equipped kitchen & private deck/courtyard. Washer/dryer. Convenient walk to cafes & restaurants, Whole Foods, MBTA, Freedom Trail, Bunker Hill Monument, USS Constitution. Courtyard is broken down Dec-March & NO smoking in house and NO smoking in courtyard. Not suitable for children under 6 years old.

Top Guest favourite
Condo in Beacon Hill
4.97 out of 5 average rating, 362 reviews

Gorgeous Beacon Hill 1BR | 1BA

Come stay at our lovely condo in the heart of Boston's most desirable neighborhood, Beacon Hill! Our newly renovated 1 bedroom | 1 bathroom condo comfortably sleeps three adults and comes with everything you need for an enjoyable stay. Whether you want to walk the Freedom Trail, visit a relative at Mass General, or shop on Newbury St, you will find it all within walking distance. You could not be more centrally located to take in all the city has to offer.

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.
Apartment in South End
4.9 out of 5 average rating, 69 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
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.
Condo in Boston
4.88 out of 5 average rating, 158 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
The living area features a neutral-toned sofa paired with a decorative throw pillow. Natural light filters through large windows, illuminating a patterned area rug. A small side chair and a sleek television are positioned nearby, enhancing the room's contemporary design.
Condo in Downtown
4.97 out of 5 average rating, 190 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

Quick stats about holiday rentals in Bay Village

  • Total holiday rentals

    Explore 230 holiday rentals in Bay Village

  • Verified guest reviews

    Over 11,420 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Bay Village holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Bay Village rentals

  • 4.6 Average rating

    Bay Village stays receive an average rating of 4.6 out of 5 from guests

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