Best Vacation Homes in Telegraph Hill
New
Apartment
6.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
Fireplace/Heating
Air Conditioner
Internet
Child Friendly
£331/Night
7 Nights - £2,316
House
10.0(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1194.79 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
£1,063/Night
7 Nights - £7,437
House
9.4(1409 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Balcony/Terrace
Parking- Air Conditioner
£97/Night
7 Nights - £675
New
Apartment
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
Pool
Ocean View- Balcony/Terrace
£1,562/Night
7 Nights - £10,931
Apartment
10.0(4 Reviews)
3 Bedrooms
2 Baths
7 Guests
1345.49 ft²
- Fireplace/Heating
Breakfast- Parking
- Air Conditioner
£729/Night
7 Nights - £5,102
Apartment
3 Bedrooms
2 Baths
10 Guests
1399 ft²
- Fireplace/Heating
Kitchen- Parking
- Air Conditioner
£879/Night
7 Nights - £6,154
New
Apartment
1 Bedroom
2 Baths
6 Guests
1593 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
£752/Night
7 Nights - £5,267
Apartment
3 Bedrooms
2 Baths
10 Guests
1206 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£726/Night
7 Nights - £5,085
Telegraph Hill Luxury Rentals
Hotel
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
Unlock the Best Price
£7,192/Night
7 Nights - £50,342
Hotel
1 Bath
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
£6,507/Night
7 Nights - £45,552
£6,500/Night
7 Nights - £45,498
£4,185/Night
7 Nights - £29,292
Hotel
4 Baths
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
£3,921/Night
7 Nights - £27,445
Hotel
4 Baths
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
£3,767/Night
7 Nights - £26,368
Hotel
4 Baths
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
£2,952/Night
7 Nights - £20,663
Telegraph Hill Pet Friendly Vacation Rentals
Condo
10.0(34 Reviews)
2 Bedrooms
1 Bath
7 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
£568/Night
7 Nights - £3,976
Apartment
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
4650.01 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
£1,237/Night
7 Nights - £8,657
Hotel
9.8(1001 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
£562/Night
7 Nights - £3,932
Condo
10.0(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£474/Night
7 Nights - £3,320
Apartment
10.0(2 Reviews)
1 Bedroom
2 Baths
6 Guests
1194.79 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Parking
£326/Night
7 Nights - £2,282
Apartment
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
£930/Night
7 Nights - £6,507
Apartment
10.0(12 Reviews)
1 Bedroom
1 Bath
2 Guests
1050 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£247/Night
7 Nights - £1,732
Condo
10.0(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Breakfast
- Pet Friendly
- Kitchen
£640/Night
7 Nights - £4,479
Telegraph Hill Large Vacation Homes
House
4 Bedrooms
2 Baths
12 Guests
1900 ft²
Private Pool
Oceanfront
Hot Tub- Fireplace/Heating
£435/Night
7 Nights - £3,046
Apartment
10.0(2 Reviews)
3 Bedrooms
3 Baths
10 Guests
904.17 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
£256/Night
7 Nights - £1,789
House
10.0(117 Reviews)
3 Bedrooms
3 Baths
10 Guests
2506 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
£919/Night
7 Nights - £6,435
Apartment
10.0(1 Review)
4 Bedrooms
4 Baths
11 Guests
631.48 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
£156/Night
7 Nights - £1,092
House
10.0(31 Reviews)
6 Bedrooms
4 Baths
18 Guests
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
£1,037/Night
7 Nights - £7,260
Apartment
10.0(30 Reviews)
3 Bedrooms
1 Bath
13 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£479/Night
7 Nights - £3,354
House
10.0(27 Reviews)
4 Bedrooms
2 Baths
13 Guests
1800 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
£942/Night
7 Nights - £6,596
Apartment
10.0(19 Reviews)
3 Bedrooms
1 Bath
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
£340/Night
7 Nights - £2,380
Why Choose Rent By Owner for your Telegraph Hill Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Telegraph Hill Vacation Rentals
Where are the best neighborhoods to stay in Telegraph Hill?
Discover the charm of Telegraph Hill, Boston, Massachusetts, by choosing a neighborhood that offers both convenience and character. When you stay in this vibrant area, you'll enjoy easy access to local amenities and picturesque surroundings, making it an ideal base for exploring the city. Whether you're seeking a peaceful retreat or a lively atmosphere, Telegraph Hill provides a variety of vacation rentals that cater to your preferences. Experience the authentic Boston lifestyle while enjoying the comfort and reliability of well-appointed accommodations in this sought-after neighborhood.
South Boston
Here, you can enjoy a lively neighborhood known for its unique local culture and convenient access to the waterfront, making it an ideal area for exploring Boston's vibrant atmosphere. This destination offers a variety of vacation rentals that provide both comfort and proximity to the region's attractions.
View 31+ Rentals in South BostonColumbus Park - Andrew Square
Located in the heart of the city, this area is perfect for those seeking easy access to public transportation and urban amenities. Staying here places you within reach of key parts of Boston, enhancing your overall experience in the region.
View 3522+ Rentals in Columbus Park - Andrew SquareCity Point
This neighborhood boasts scenic views and a relaxed atmosphere, making it a great choice for travelers looking to enjoy the quieter side of the city. The vacation rentals available here offer a peaceful retreat while still being close to Boston's downtown attractions.
View 2456+ Rentals in City PointBest Times to Visit Telegraph Hill
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination can enhance your experience, as seasonal variations in the region offer different opportunities for enjoying its unique atmosphere and local events.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, the region experiences warm temperatures and longer days, making it perfect for exploring outdoor attractions from your vacation rentals.
Average Temperature Daytime: 70-78°F - Nighttime: 55-65°F
Early Fall (September to October)
This period offers mild weather with vibrant fall foliage, providing a scenic backdrop for your stay in this destination's charming neighborhood.
Average Temperature Daytime: 68-75°F - Nighttime: 50-60°F
Off-Season Highlights
Winter (December to February)
The winter months see cooler temperatures and fewer visitors, offering a quieter experience for those staying in vacation rentals and seeking peaceful surroundings.
Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F
Late Fall (November)
As the region transitions into winter, the weather cools down, creating a cozy atmosphere ideal for enjoying the local ambiance in your rental accommodations.
Average Temperature Daytime: 50-58°F - Nighttime: 40-45°F
Weekly Weather Forecast for Telegraph Hill
How to Book Your Telegraph Hill Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Telegraph Hill
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to private or shared outdoor seating areas with scenic views of the city or harbor.
- Take advantage of well-maintained outdoor patios or decks ideal for relaxing or entertaining guests.
- Experience convenient outdoor parking options, often included with your stay in this region.
- Find properties with lush gardens or landscaped lawns that add a touch of nature to your vacation experience.
- Look for rentals offering outdoor grilling facilities, perfect for al fresco dining in the area.
- Stay connected to nearby walking trails or parks that allow you to explore the natural beauty here.
- Benefit from spacious balconies or terraces that provide unique vantage points over the local skyline or water views.
Top Attractions Around Telegraph Hill
What attractions are nearby?
Within this vibrant neighborhood, you can enjoy a variety of nearby activities, including exploring historic sites, strolling through scenic parks, and discovering charming local eateries that showcase the region's rich cultural heritage.
Family Activities
- Boston Children’s Museum: Engage your family in interactive exhibits and hands-on activities designed to inspire curiosity and learning for visitors staying nearby.
- Harborwalk: Enjoy a scenic stroll along the Boston Harbor, where you can take in beautiful views and participate in family-friendly events happening in this lively waterfront area.
- Rose Kennedy Greenway: Spend quality time outdoors exploring gardens, open spaces, and kid-friendly installations set amidst the bustling cityscape.
- North End Food Tour: Introduce your family to the region’s rich culinary heritage with a guided walk through historic streets filled with authentic Italian eateries and markets.
Adult Activities
- Harborwalk Strolls: Take a leisurely walk along the historic harbor, enjoying scenic views and vibrant maritime activity.
- Local Fine Dining: Dine at renowned restaurants in the area that showcase the region’s fresh seafood and local flavors.
- Art and Cultural Tours: Explore galleries and cultural institutions nearby that highlight the area's artistic heritage.
- Scenic Lookouts: Visit panoramic viewpoints offering breathtaking vistas of the Boston skyline and waterfront, perfect for memorable photos.
Other Places to Stay in Telegraph Hill, MA
Bunker Hill Monument
L Street Beach
South Boston
Telegraph Hill Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining: Take advantage of nearby eateries to experience the authentic flavors that make this area a culinary hotspot.
- Plan Scenic Walks: Discover the charm of the neighborhood by walking through scenic routes that offer stunning views and photo opportunities.
- Visit Local Landmarks: Make time for prominent local landmarks to immerse yourself in the rich history and culture of the region.
- Utilize Public Transit: Use accessible public transportation options to conveniently explore the surrounding neighborhoods and attractions.
Transportation Options
- Boston Transit System (MBTA): The region’s comprehensive subway and bus network offers convenient access to and from Telegraph Hill, making it easy for you to explore the city efficiently.
- Commuter Rail Services: Connecting this area to surrounding suburbs and other regional destinations, commuter rails provide a reliable transportation option for day trips and commuting needs.
- Taxi and Rideshare Options: Taxis and rideshare services like Uber and Lyft are readily available here, offering flexible transportation right at your doorstep for local travel convenience.
- Walking and Biking: With its pedestrian-friendly streets and scenic paths, exploring the neighborhood on foot or by bike allows you to enjoy the area's charm intimately and effortlessly.
Local Customs Options
- Clam Chowder Tradition: Locals take pride in their traditional New England clam chowder, which you can often enjoy at neighborhood eateries that reflect the culinary heritage of the region.
- Festivals and Parades: Celebrating community spirit, seasonal festivals and parades are common here, offering an authentic glimpse into local customs and history.
- Historical Preservation: Respect for historical buildings and landmarks is deeply rooted, with residents actively maintaining the area's unique architectural charm.
- Harbor Activities: Participating in or observing maritime traditions, such as sailing and fishing, forms a vital part of the cultural fabric here, connecting residents and visitors alike to the region’s maritime legacy.
Frequently Asked Questions About Telegraph Hill?
1. What are the top vacation rentals in Telegraph Hill?
There are a lot of options in Telegraph Hill. If you plan on staying in the Telegraph Hill area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Telegraph Hill:
- Boston Yacht Haven Inn & Marina
- Best of Boston Houseboat Heat/AC in Boston Harbor Suite1 in Historic Navy Yard
- Historic Home At Freedom Trail
- Historic Townhouse Condo in the center of Boston, across from the Public Garden
- "Travelers Choice Award" Spacious 2BD/2Bath Heat/AC 45 ft yacht Freedom Trail
- Charming House In Downtown Boston, Nearby Attractions, Parking & Free WiFi
- Stunning South End/Back Bay Penthouse!
- Chic South End Studio With Patio
- Great South End/Back Bay location, 1 bed condo near T station
- Fully Furnished Luxury Oceanfront Residence Temporary & Relocation Housing
2. How many vacation rentals have private pools in Telegraph Hill?
There are 39 vacation rentals with private pools near Telegraph Hill. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Telegraph Hill are best for families?
If you are looking for a family-friendly vacation home in Telegraph Hill, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Telegraph Hill:
4. How many Rentbyowner vacation rentals are available in Telegraph Hill?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 3216 in the Telegraph Hill area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Telegraph Hill.
5. What is the cancellation policy for vacation rentals in Telegraph Hill, Boston?
Cancellation policies vary depending on the property listing. You should review the specific terms and conditions outlined in the rental listing or contact the property owner directly to understand the cancellation options available.
6. How do I ensure my booking in this region is secure and reliable?
Booking through a trusted platform provides added security. Make sure to read reviews, verify property details, and communicate directly with the host if you have any concerns before confirming your reservation.
7. Are there any additional fees I should be aware of when booking here?
Additional fees such as cleaning, service charges, or taxes may apply. Details will be specified in each listing, so it’s best to review the fee breakdown before completing your reservation.
8. What amenities are typically included in vacation rentals in this area?
Amenities vary by property, but common features include Wi-Fi, fully equipped kitchens, and laundry facilities. To see what’s included, check the property description or reach out directly to the host.
9. Is there parking available for vacation rentals near here?
Parking availability depends on the specific property. Some listings include private parking, while others may require street parking or nearby garage access. Confirm parking arrangements with the host prior to booking.
Telegraph Hill Top Rated Vacation Rentals
Hotel
10.0(2 Reviews)
4 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
£988/Night
7 Nights - £6,916
Hotel
10.0(2 Reviews)
2 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
£704/Night
7 Nights - £4,929
Hotel
10.0(2 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
£346/Night
7 Nights - £2,423
House
10.0(1 Review)
6 Bedrooms
4 Baths
11 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
£2,212/Night
7 Nights - £15,486
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
7 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
£1,403/Night
7 Nights - £9,821
Hotel
10.0(1 Review)
4 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
£1,327/Night
7 Nights - £9,289
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
5 Guests
750 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
£1,119/Night
7 Nights - £7,830
Hotel
10.0(1 Review)
3 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
£1,045/Night
7 Nights - £7,315
