
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.

Walk! Walk! Kenmore Square - 2 Beds / 1 Bathroom
2 beds / 1 bathroom apartment in the middle of everything! Located right in Kenmore Square, steps from subway station and Famous Citgo Sign. Walking distance to Fenway Park, Back Bay, restaurants, bars, and more! Walk walk walk everywhere! Next to Boston University and in front of Charles River Esplanade. Very close to Downtown, Cambridge, Longwood Medical Area, supermarkets, and way so many cool places! Includes everything you'll need for your stay. Super safe and convenient neighborhood! :)

North End/TD Garden Condo w/Rooftop Deck
Your own condo in the heart of Boston’s historic North End. Walk to Quincy Market, the Aquarium, the Greenway, TD Garden, Harborwalk, dozens of shops and eateries, the Old North Church and the Freedom Trail. Private rooftop deck, full kitchen, antenna and wireless. No doors but three areas, two rooms separated by a galley kitchen. The stairwell is in the middle of the space and the floor mattress is near that and across from the galley kitchen. Fourth floor walk up and well worth the climb.

Remodeled Suite w/ Roof Deck & Views
- Escape on our Private Rooftop deck - Parking! - Just a short walk away from new Gilman sq. T stop- .3 mile 8 min walk. - Minutes drive to downtown Boston - Located just a few blocks outside of Union Square, Somerville. 5 mile/ 10 min walk to new Union Square T -5min drive - 7min bike ride to Harvard University, close to MIT or Tufts University. 25min walk to Harvard. -1 gig high speed WiFi -Kitchenette with Fridge, Keurig + drip coffee makers, Toaster, Microwave & sink for light meals.

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.

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!

Boston Rooftop Retreat
A beautiful, fully renovated historic brownstone with a private rooftop deck overlooking the city. Come be inspired by this colorful and romantic artist studio filled with books, records, art and all the comforts of home in a quiet neighborhood with lovely views. Conveniently located a short walk from public transportation, world class universities, medical institutions and museums. About a 22 minute walk to Fenway Park, MGM Music Hall and other great attractions!

Second Oldest Home in Beacon Hill
Small private studio apartment built in 1789, located at the top of Beacon Hill. It is next door to the oldest house in Beacon Hill and is close to many tourist attractions while still being in a quiet local neighborhood. You will be with in 5 minutes of the Massachusetts State House and the oldest park in the country known as the Boston Common. You will also be within walking distance of Back Bay and the North End. We welcome you to our small home in Beacon Hill.

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.

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.

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

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.

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
Other great holiday rentals in Downtown

A Lovely Private Room in the heart of Cambridge

Central Penthouse & balcony in Boston Chinatown

(MGH9-4) Bright Beacon Hill Studio

Large Private Bedroom & Bathroom by the Seaport

Private Bedroom in Beacon Hill (Bedroom #1)

Beacon Hill, J. Miller Flats - 1 Bedroom Flat #2

Historic Mayor’s Mansion #1

Beacon Hill MGH Close to Acorn St, Outdoor space*
When is the best time to visit Downtown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 122 | € 122 | € 156 | € 179 | € 201 | € 215 | € 203 | € 205 | € 201 | € 181 | € 160 | € 142 |
| 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
1,030 of Downtown holiday rentals include wifi 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
- Hotel rooms Downtown
- Pet-friendly rentals Downtown
- Rentals with breakfast Downtown
- Rentals with outdoor seating Downtown
- Apartment rentals Downtown
- Family-friendly rentals Downtown
- Rentals with pools Downtown
- Rentals with a patio Downtown
- Serviced apartment rentals Downtown
- Rentals with an EV charger Downtown
- Rentals with a fireplace Downtown
- Fitness-friendly rentals Downtown
- Rentals with a washing machine and dryer Downtown
- House rentals Downtown
- Flat rentals Downtown
- Hampton Beach
- TD Garden
- Fenway Park
- Harvard University
- Boston Common
- Revere Beach
- Brown University
- Freedom Trail
- New England Aquarium
- MIT Museum
- Boston University
- Boston Seaport
- Canobie Lake Park
- Crane Beach
- Boston Convention and Exhibition Center
- Duxbury Beach
- Museum of Fine Arts
- Quincy Market
- Gillette Stadium
- Onset Beach
- North Hampton Beach
- Prudential Center
- Roger Williams Park Zoo
- Roxbury Crossing Station
- Things to do Downtown
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- Nature and outdoors Massachusetts
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