Vacation Rentals in Telegraph Hill, MA: Compare 10+ Sites & Save

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  4.  Massachusetts

  5.  Boston
  6.  Telegraph Hill

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2294 Best Vacation Rentals in Telegraph Hill (Starting from $36)

Southie 3BD 1BA near Seaport and Convention Center BECE
Southie 3BD 1BA near Seaport and Convention Center BECE
Apartment
Boston, MA, USA
0.1k from Telegraph Hill center

Apartments, Accommodations, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$620
Average price / night
Check Availability
Heart of Southie - Hot Tub + Walk to Top Bars
Heart of Southie - Hot Tub + Walk to Top Bars
House
Boston, MA, 02127, United States
0.4k from Telegraph Hill center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

4 Bedrooms13 Guests
10.0

Exceptional

23 reviews

$1416
Average price / night
Check Availability
South Boston Dream 5BD/2Bath w/Sky Deck Near Airport
South Boston Dream 5BD/2Bath w/Sky Deck Near Airport
House
Boston, MA, 02127, United States
0.5k from Telegraph Hill center

AC, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Patio, TV

5 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$1513
Average price / night
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Bright Private Room Near Beaches, Public Transit
Bright Private Room Near Beaches, Public Transit
Apartment
Boston, MA, USA
0.4k from Telegraph Hill center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$1890
Average price / night
Check Availability
Newly renovated 3 bed 3.5 bath townhouse close to beach, seaport and downtown
Newly renovated 3 bed 3.5 bath townhouse close to beach, seaport and downtown
House
Boston, MA, 02127, United States
0.6k from Telegraph Hill center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$1393
Average price / night
Check Availability
4BR 1BH Apt in South Boston near Old Harbor Beach
4BR 1BH Apt in South Boston near Old Harbor Beach
Apartment
Boston, MA, USA
0.4k from Telegraph Hill center

Apartments, Accommodations, Lodgings, Vacation rentals, Places to stay, Beach rentals

4 Bedrooms2 Guests
5.7

Review score

43 reviews

$172
Average price / night
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Modern 5BD3B in Boston Steps to Convention Center
Modern 5BD3B in Boston Steps to Convention Center
House
Boston, MA, 02127, United States
0.6k from Telegraph Hill center

AC, Dryer, Heater, Laundry, No Smoking, Washer

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1461
Average price / night
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Quarters on DOT by Thatch
Quarters on DOT by Thatch
Apartment
Boston, MA, USA
0.5k from Telegraph Hill center

Apartments, Accommodations, 3-star, Lodgings, Vacation rentals, Places to stay, Beach rentals

14 Bedrooms28 Guests
7.0

Good

212 reviews

$36
Average price / night
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New Reno! 3 Beds, in unit Washer & Dryer, Southie!
New Reno! 3 Beds, in unit Washer & Dryer, Southie!
Apartment
Boston, MA, 02127, United States
0.7k from Telegraph Hill center

AC, Dryer, Heater, Internet, Laundry, Microwave, No Smoking, TV, Washer

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$335
Average price / night
Check Availability
Sunny convenient home w/private patio! Easy walk to everything!
Sunny convenient home w/private patio! Easy walk to everything!
Apartment
Boston, MA, USA
0.7k from Telegraph Hill center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay, Self-catering

1 Bedroom4 Guests
7.2

Good

4 reviews

$435
Average price / night
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Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
House
Boston, MA, 02127, United States
0.7k from Telegraph Hill center

AC, Balcony, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.8

Exceptional

186 reviews

$574
Average price / night
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Easy Commute South Boston 4BR 1BTH Apartment
Easy Commute South Boston 4BR 1BTH Apartment
Apartment
Boston, MA, USA
1.0k from Telegraph Hill center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$1890
Average price / night
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Clean and convenient w/ patio! Walk to Boston highlights!
Clean and convenient w/ patio! Walk to Boston highlights!
Apartment
Boston, MA, 02127, United States
0.7k from Telegraph Hill center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

1 Bedroom4 Guests
9.4

Superb

44 reviews

$381
Average price / night
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Southie Living by Seaport, Red Line, Beach & Bars
Southie Living by Seaport, Red Line, Beach & Bars
Apartment
Boston, MA, USA
1.0k from Telegraph Hill center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$1890
Average price / night
Check Availability
Blueground | S. Boston, w/d, balcony, nr ICA
Blueground | S. Boston, w/d, balcony, nr ICA
Apartment
Boston, MA, 02127, United States
0.8k from Telegraph Hill center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$184
Average price / night
Check Availability
2 Mi to Dtwn: Boston Apartment Near Beaches!
2 Mi to Dtwn: Boston Apartment Near Beaches!
Apartment
Boston, MA, 02127-3233, United States
0.8k from Telegraph Hill center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

1 Bedroom2 Guests
9.6

Exceptional

11 reviews

$461
Average price / night
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Easy Commute South Boston 4BR 1BH Apt
Easy Commute South Boston 4BR 1BH Apt
Apartment
Boston, MA, USA
1.0k from Telegraph Hill center

Apartments, Accommodations, Lodgings, Vacation rentals, Places to stay, Self-catering, Beach rentals

8 Bedrooms16 Guests
6.5

Good

71 reviews

$145
Average price / night
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Newly Renovated 2 Bedroom in Southie!
Newly Renovated 2 Bedroom in Southie!
House
Boston, MA, 02127, United States
0.9k from Telegraph Hill center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

2 Bedrooms4 Guests
New to Booking
$321
Average price / night
Check Availability
Lovely Two Bedroom Condo in South Boston
Lovely Two Bedroom Condo in South Boston
Apartment
Boston, MA, USA
1.2k from Telegraph Hill center

Apartments, Accommodations, Lodgings, Vacation rentals, Places to stay, Self-catering, Beach rentals, Condos

2 Bedrooms6 Guests
8.1

Very Good

39 reviews

$391
Average price / night
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Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
Huge Single Family Retreat-Work-Vacation-Near Convention Center & South Station
House
Boston, MA, 02127, United States
1.0k from Telegraph Hill center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

6 reviews

$1280
Average price / night
Check Availability
S Boston 1BR w Doorman WD nr Seaport BOS-189
S Boston 1BR w Doorman WD nr Seaport BOS-189
Apartment
Boston, MA, USA
1.2k from Telegraph Hill center

Tv, Guest Services, Business Services, Accessibility, Wellness Facilities, Internet, Pet Friendly

1 Bedroom2 Guests
New to Booking
$183
Average price / night
Check Availability
Private Parking! 4BR Family Home in South Boston
Private Parking! 4BR Family Home in South Boston
House
Boston, MA, 02127, United States
1.2k from Telegraph Hill center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1437
Average price / night
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Southie! 2Bedroom, Washer/Dryer in unit!
Southie! 2Bedroom, Washer/Dryer in unit!
Apartment
Boston, MA, 02127, United States
1.2k from Telegraph Hill center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

2 Bedrooms4 Guests
6.0

Review score

1 reviews

$335
Average price / night
Check Availability
Modern 2 BR, 1BA Near Convention Center & Seaport
Modern 2 BR, 1BA Near Convention Center & Seaport
Apartment
Boston, MA, 02127, United States
1.2k from Telegraph Hill center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
9.8

Exceptional

209 reviews

$328
Average price / night
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New 3 beds in Southie! W/D in unit.
New 3 beds in Southie! W/D in unit.
House
Boston, MA, 02127, United States
1.3k from Telegraph Hill center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

1 Bedroom4 Guests
8.0

Good

1 reviews

$335
Average price / night
Check Availability
Spacious Residence near Seasport
Spacious Residence near Seasport
Apartment
Boston, MA, 02127, United States
1.3k from Telegraph Hill center

AC, Dryer, Internet, Laundry, No Smoking, Washer

2 Bedrooms90 Guests
New to Booking
$643
Average price / night
Check Availability
Boston Modern LUX - Subway / Family / Business Ready
Boston Modern LUX - Subway / Family / Business Ready
Apartment
Boston, MA, 02127, United States
1.3k from Telegraph Hill center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, TV, Washer

5 Bedrooms14 Guests
New to Booking
$1761
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Telegraph Hill.

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Frequently Asked Questions

You can explore 2294 verified vacation rentals in Telegraph Hill. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Telegraph Hill vary depending on the season, property size, and location. Rates typically start from around $36 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Telegraph Hill include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Telegraph Hill welcome pets. Currently, 56 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Telegraph Hill often include amenities such as Fireplace/Heating, Laundry, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.