Telegraph Hill holiday lettings
We found 44 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Telegraph Hill that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for spending time at your holiday home, which might include parking and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Telegraph Hill

The Heart of Southie (Garage + Roof Deck)
Sleeps 9 · 2 bedrooms · 2 bathrooms
10 out of 10
exceptional
(40 reviews)
Top rated rentals - Telegraph Hill

Boston Baby was the best trip for me and my three sisters from Edinburgh, Scotland.
9.8 out of 10
exceptional
(173 reviews)
Thanks you Jack for having us to stay. Your apartment was huge. 4 beds. 3 bathrooms. In the best neighbourhood. We loved where we stayed. And so close to everything. Couldn't recommend this apartment so much Couldn't recommend the
steph C.
Stayed Jun 2025
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
More holiday ideas
More holiday ideas
- Bed and breakfasts in Great Brook Farm State Park
- Ski-In/Ski-Out rentals near Great Brook Farm State Park
- Chalets in Dorchester Shores Reservation
- Bed and breakfasts in Lowell Heritage State Park
- Rv and caravan rentals in Lowell Heritage State Park
- Villas in Hemlock Gorge Reservation
- Mountain rentals near Hemlock Gorge Reservation
- Apartments in Natural Resources Trust of Easton
- Castles in Beaver Brook Reservation
- Villas in Beaver Brook Reservation
- Apartments in Brookline
- Houses in Brookline
- Bed and breakfasts in Noon Hill
- Monthly rentals in Essex
- Bed and breakfasts in Belle Isle Marsh Reservation
- Apartments in Natick
- Houses in Natick
- Monthly rentals in Natick
- Apartments in Fenway Park
- Apartments in Boston
- Beach rentals in Boston
- Houses in Boston
- Oceanfront rentals in Boston
- Castles in Greycourt State Park
- Rv and caravan rentals in Governor Hutchinson's Field
- Ski-In/Ski-Out rentals near Governor Hutchinson's Field
- Apartments in Peabody
- Monthly rentals in Somerville
- Apartments in Foxboro
- Monthly rentals in Foxboro
- Apartments in East Cambridge
- Rv and caravan rentals in Shattuck Reservation
- Apartments in Massachusetts
- Beach rentals in Massachusetts
- Cottages in Massachusetts
- Pet-Friendly rentals in Massachusetts
- Houses in Massachusetts
- Lake rentals in Massachusetts
- Cabins in Massachusetts
- Oceanfront rentals in Massachusetts
- Villas in Massachusetts
- Monthly rentals in Massachusetts
- Monthly rentals in Gloucester
- Castles in Ipswich River
- Rv and caravan rentals in Quincy Shore Reservation
- Cottages in Westford
- Lake rentals in Westford
- Cottages in Boston
- Pet-Friendly rentals in Boston
- Houseboats in Boston
- Cabins in Boston
- Villas in Boston
- Monthly rentals in Boston (and vicinity)
- Guest houses in Roxbury Heritage State Park
- Bed and breakfasts in Stony Brook Wildlife Sanctuary
- Ski-In/Ski-Out rentals near Stavros Reservation
- Resorts in Constitution Beach State Park
- Castles in Myles Standish Monument State Reservation
- Apartments in Danvers
- Houses in Danvers
- Townhouses in Danvers
- Bed and breakfasts in Stoddard Park
- Apartments in Beacon Hill
- Houses in Beacon Hill
- Apartments in Charles River Esplanade
- Apartments in Boston
- Hotels in Boxford State Forest
- Bed and breakfasts in Southwest Corridor Park
- Apartments in Alewife Brook Reservation
- Bed and breakfasts in Bridge Island Meadows
- Castle Island Holiday Rentals
- Downtown Boston Holiday Rentals
- Rowes Wharf Holiday Rentals
- Boston Financial District Holiday Rentals
- Leader Bank Pavilion Holiday Rentals
- Boston Medical Center Holiday Rentals
- Columbus Park - Andrew Square Holiday Rentals
- D Street - West Broadway Holiday Rentals
- Seaport District Holiday Rentals
- Shawmut Holiday Rentals
- University of Massachusetts Boston Holiday Rentals
- Pleasure Bay Beach Holiday Rentals
- Boston Convention and Exhibition Center Holiday Rentals
- Flynn Cruiseport Boston Holiday Rentals
- South Boston Holiday Rentals
- City Point Holiday Rentals
- Seaport World Trade Center Holiday Rentals
- Harrison Lenox Holiday Rentals
- Boston Holiday Rentals
- Boston Design Center Holiday Rentals
- South of Washington Holiday Rentals
- Savin Hill Station Holiday Rentals
- Liberty Wharf Holiday Rentals
- South Station Holiday Rentals
- M Street Beach Holiday Rentals
- Tufts Medical Center Holiday Rentals
- John F. Kennedy Presidential Library and Museum Holiday Rentals
- Blackstone Block Historic District Holiday Rentals
- Boston JFK-UMass Station Holiday Rentals
- Carson Beach Holiday Rentals