
Holiday houses in Downtown
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Top-rated holiday rentals in Downtown
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

Penthouse 2 Beds /2 Baths luxury in South Boston
Kick back and relax in this calm, stylish space. You won’t even feel like you are in the center of the city . Everything you need is within a walking distance , bars , coffee shops and many restaurants to choose from. Top floor unit, private balcony with 2 full bedrooms & 2 full bathrooms on opposite sides of the house makes traveling in groups much more comfortable. Brand new build 2023 , this is a hotel like stay professionally managed but with the comfort of a home away from home

Large Loft Steps From Boston Common | Short Stays
This 3 Bed, 2 Bath apartment with Laundry in unit is available for both long and short term rental. Operated by Remedy Homes, a provider of short term medical stays, this beautifully designed and furnished loft is located right in the heart of Boston. Two Queen beds and one Full Sized Bed and two full bathrooms. The unit is on the 3rd floor and is completely accessible by a self-check-in, meaning you will be able to minimize exposure. On-site security and 2 elevators is a big plus!

BEAUTIFUL BEACON HILL 2 BEDROOM!
Come stay at our charming condo in the heart of Boston's most desirable neighborhood, Beacon Hill! Our two bedroom/one full-bath condo is beautifully furnished and comes with everything you need for an enjoyable stay. Whether you want to walk the Freedom Trail, jump on a Duck Boat Tour, visit a relative at Mass General, shop on Newbury St, or dine on Charles 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.

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.

Cozy Back Bay Boston Retreat!
There is not a better location in the city with quick and easy access to everything Boston has to offer, as well as the neighboring communities. You will find the space to be a little sanctuary away from the hustle and bustle of city life whether you are in Boston for work or leisure. Much like rest of Back Bay, the space and finishes have a Victorian era feel with some updates made throughout the decades. I hope you can relax and feel at home!

Sunny & Spacious w/FREE parking near Kendall/MIT
Sunny, immaculate & special apartment located in Kendall/E. Cambridge w/700 sq. ft and free parking. This 3rd floor, wood and nature inspired space is perfect for anyone seeking a productive & comfy setting. Welcome basket, plush bedding, & wifi w/separate work space included. Walking distance to Kendall & Lechmere trains. Steps from vibrant Kendall Sq., MIT, Galleria Mall, MOS, Charles River & lots of restaurants.

Beacon Hills Studio next to State house
Come stay at our lovely studio in the heart of Boston's most desirable neighborhood, Beacon Hill! Whether you want to walk the Freedom Trail, or shop on Newbury St, Surrounded by brownstones, coffee shops, and locals, you’ll feel right at home in this community. Steps away from the State House, MGH, and the Boston Common, You could not be more centrally located to take in all the city has to offer.

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.

Stylish Boston Getaway | Rooftop & Fireplace
Welcome to your Boston retreat! This stylish 1-bedroom on a charming cobblestone street offers comfort and unbeatable walkability. Enjoy the quiet Bay Village residential feel while being just steps from the Back Bay, South End, Chinatown and Theater District. Start your day with coffee on the shared rooftop or unwind by the fireplace after exploring the city.

North End 2 BR | 1 BA Duplex in Little Italy
Newly renovated 2 Bedroom | 1 Bath garden-level duplex is located in Boston's historic North End. This spacious 850 sqft condo is located on the ground floor and basement and offers central A/C, brand new kitchen and bath, lots of space, and new hardwood floors. We are steps to the waterfront and to all the great Italian restaurants!!

King Bed Loft in the Heart of Downtown Boston
Welcome to our spacious, 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! Enjoy the newly tiled bathroom and a super comfortable king bed with 100% cotton linens.
Popular amenities for Downtown holiday rentals
Other great holiday rentals in Downtown

A Lovely Private Room in the heart of Cambridge

5-min walk to Prudential Ctr & 3 blocks to Fenway

AKBrownstone: Loft rooftop views by T

Historic Mayor’s Mansion #1

Cozy Somerville Room (Near MBTA/Bike Path)

Home on quiet street near Harvard

Modern Brownstone - walk to Longwood Medical Area!

Gorgeous Beacon Hill 1BR | 1BA
When is the best time to visit Downtown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $245 NZD | $245 NZD | $313 NZD | $360 NZD | $404 NZD | $431 NZD | $407 NZD | $411 NZD | $404 NZD | $490 NZD | $338 NZD | $260 NZD |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
Quick stats about holiday rentals in Downtown

Total holiday rentals
Explore 1,030 holiday rentals in Downtown

Verified guest reviews
Over 53,560 verified reviews to help you choose

Family-friendly holiday rentals
300 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 460 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
670 properties have a dedicated workspace

Wi-Fi availability
1,030 of Downtown holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Downtown rentals

4.6 Average rating
Downtown stays receive an average rating of 4.6 out of 5 from guests

Nearby attractions
Downtown's top spots, include Boston Common, New England Aquarium, and Boston Public Garden
Destinations to explore
- Rentals with an EV charger Downtown
- Fitness-friendly rentals Downtown
- Rentals with a washing machine and dryer Downtown
- Rentals with pools Downtown
- Rentals with breakfast Downtown
- Condo rentals Downtown
- Rentals with a patio Downtown
- Family-friendly rentals Downtown
- Hotel rooms Downtown
- Rentals with outdoor seating Downtown
- Pet-friendly rentals Downtown
- Apartment rentals Downtown
- Rentals with a fireplace Downtown
- House rentals Downtown
- Serviced apartment rentals Downtown
- Hampton Beach
- TD Garden
- Fenway Park
- Boston Common
- Harvard University
- Revere Beach
- Brown University
- MIT Museum
- New England Aquarium
- Boston University
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Boston Seaport
- Duxbury Beach
- Boston Convention and Exhibition Center
- Museum of Fine Arts
- Quincy Market
- Onset Beach
- North Hampton Beach
- Prudential Center
- Roger Williams Park Zoo
- Roxbury Crossing Station
- Boston Children's Museum
- Things to do Downtown
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