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Holiday homes in Chelsea You’ll Love

Top-Rated Chelsea Holiday homes for Every Budget and Style!

Looking for a holiday home in Chelsea (Massachusetts)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $53.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Chelsea.

We found 31 Holiday-homes in Chelsea and the surrounding area (within 20 miles)

Revere Luxury House, Private Beach in Revere, USA

Revere Luxury House, Private Beach

Villa in Revere near Chelsea, Massachusetts , 115 Lynnway
Providing a garden, Revere Luxury House, Private Beach offers accommodations in Revere.
  • Parking
  • Pets allowed
  • Family rooms

no reviews

from $309.15 Show details »

Modern Single Family Home minutes from Fort hill in Boston, USA

Modern Single Family Home minutes from F...

Holiday home in Boston near Chelsea, Massachusetts , 5 Hilton Terrace
A recently renovated vacation home, Modern Single Family Home minutes from Fort hill offers accommodations in Boston.
  • Parking

Fabulous 20 Reviews 8.7

from $348.41 Show details »

Modern Townhome,boston Vacation,2 Bath,pkg,deck in Brookline, USA

Modern Townhome,boston Vacation,2 Bath,p...

Holiday home in Brookline near Chelsea, Massachusetts
Modern Townhome, boston Vacation,2 Bath, pkg,deck is located in Brookline, just 1.7 miles from Boston Museum of Fine Arts and 1.9 miles from Fenway Pa...
  • Pets allowed

Good 6 Reviews 7.9

from $467.46 Show details »

Brookline Village, Central Air, 2b, Near Longwood in Brookline, USA

Brookline Village, Central Air, 2b, Near...

Holiday home in Brookline near Chelsea, Massachusetts , 7 Harvard Square
Brookline Village, Central Air, 2b, Near Longwood is located in Brookline, just 1.7 miles from Boston Museum of Fine Arts and 1.9 miles from Fenway Pa...
  • Pets allowed

Good 3 Reviews 7.3

from $296.24 Show details »

Pvt Room, St Marys, Fenway, Longwood, Green Line in Brookline, USA

Pvt Room, St Marys, Fenway, Longwood, Gr...

Holiday home in Brookline near Chelsea, Massachusetts , 1029 Beacon Street
Pvt Room, St Marys, Fenway, Longwood, Green Line is located in Brookline, just a 10-minute walk from Boston University and 1.1 miles from Boston Museu...

Fabulous 16 Reviews 8.7

from $156.75 Show details »

Blueground Fenway 1bd apartment BOS-1110 in Boston, USA

Blueground Fenway 1bd apartment BOS-1110

Holiday home in Boston near Chelsea, Massachusetts
Blueground Fenway 1bd apartment BOS-1110 is located in Boston, just a 9-minute walk from Boston University and one mile from Boston Museum of Fine Art...
  • Pets allowed

no reviews

from $75.00 Show details »

Upscale Penthouse w Gym & Parking near MGH & TUFTS in Boston, USA

Upscale Penthouse w Gym & Parking near M...

Holiday home in Boston near Chelsea, Massachusetts , 99 Kneeland Street
Just a 12-minute walk from Boston Tea Party Ship & Museum and 0.8 miles from Back Bay, Upscale Penthouse w Gym & Parking near MGH & TUFTS features acc...
  • Parking
  • Pets allowed
  • Fitness centre

no reviews

from $68.00 Show details »

Waterfront Retreat with Deck about 7 Mi to Boston! in Winthrop, USA

Waterfront Retreat with Deck about 7 Mi...

Holiday home in Winthrop near Chelsea, Massachusetts
Waterfront Retreat with Deck about 7 Mi to Boston! offers accommodations in Winthrop, 1.1 miles from Winthrop Beach and 7.3 miles from Freedom Trail.
  • Parking

Fabulous 2 Reviews 9.0

from $55.00 Show details »

Beacon Hill: The Aldrich House in Boston, USA

Beacon Hill: The Aldrich House

Holiday home in Boston near Chelsea, Massachusetts , 59 Mount Vernon Street
Housed in a historic building, Beacon Hill: The Aldrich House features accommodations with a garden and free Wifi in Boston, a 8-minute walk from King...
  • Pets allowed
  • Bar
  • Family rooms

Exceptional 7 Reviews 9.8

from $72.00 Show details »

Luxe 3BD 2BA apt close to Downtown w Free Parking in Boston, USA

Luxe 3BD 2BA apt close to Downtown w Fre...

Holiday home in Boston near Chelsea, Massachusetts , 16R Waverly Street
Luxe 3BD 2BA apt close to Downtown w Free Parking is located in Boston, just 2 miles from Harvard University and 2.2 miles from John F.

no reviews

from $75.00 Show details »

Harvard Squares ONLY Tiny House on the Charles! in Cambridge, USA

Harvard Squares ONLY Tiny House on the C...

Holiday home in Cambridge near Chelsea, Massachusetts , 22 Hingham Street
Harvard Squares ONLY Tiny House on the Charles! offers accommodations in Cambridge, 1.6 miles from Massachusetts Institute of Technology and 2.3 miles...

no reviews

from $59.00 Show details »

Private Home Near Kendall Sq - CM-241 in Cambridge, USA

Private Home Near Kendall Sq - CM-241

Holiday home in Cambridge near Chelsea, Massachusetts , Cardinal Medeiros Avenue 241
Private Home Near Kendall Sq - CM-241 is located in Cambridge, just 1.6 miles from Peabody Museum and 1.8 miles from Harvard Square.
  • Parking
  • Pets allowed

no reviews

from $82.00 Show details »

Luxury Apartment w King Bed Shared Pool & Rooftop slp 7 in Cambridge, USA

Luxury Apartment w King Bed Shared Pool...

Holiday home in Cambridge near Chelsea, Massachusetts , 151 North First Street
Just 1.1 miles from TD Garden and 1.2 miles from Freedom Trail, Luxury Apartment w King Bed Shared Pool & Rooftop slp 7 features accommodations in Cam...
  • Pets allowed
  • Fitness centre
  • Swimming pool
  • Swimming Pool

no reviews

from $73.00 Show details »

Bright and Pet-Friendly Home 2 Mi to Harvard Square in Watertown, USA

Bright and Pet-Friendly Home 2 Mi to Har...

Holiday home in Watertown near Chelsea, Massachusetts
Bright and Pet-Friendly Home 2 Mi to Harvard Square offers accommodations in Watertown, 2.2 miles from Brattle Theatre and 2.2 miles from Harvard Squa...
  • Parking
  • Pets allowed
  • Spa and wellness centre

no reviews

from $79.00 Show details »

3BR2Bth parking, CambridgeBoston, WD, Subway, AC in Somerville, USA

3BR2Bth parking, CambridgeBoston, WD, Su...

Holiday home in Somerville near Chelsea, Massachusetts , 30 Horace Street 2 Floor
3BR2Bth parking, CambridgeBoston, WD, Subway, AC is a recently renovated vacation home in Somerville, near Inman Square.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 14 Reviews 9.6

from $500.77 Show details »

3BR2Bth parking Cambridge Boston in Somerville, USA

3BR2Bth parking Cambridge Boston

Holiday home in Somerville near Chelsea, Massachusetts , 30 Horace Street 1 Floor
3BR2Bth parking Cambridge Boston is located in Somerville, just a 14-minute walk from Inman Square and 1.2 miles from Central Square Theatre.
  • Parking
  • Pets allowed
  • Family rooms

Exceptional 10 Reviews 9.8

from $254.44 Show details »

Harvard House - 2BR Retreat adjacent to university in Cambridge, USA

Harvard House - 2BR Retreat adjacent to...

Holiday home in Cambridge near Chelsea, Massachusetts , 62 Kirkland Street
Harvard House - 2BR Retreat adjacent to university is located in Cambridge, just a 12-minute walk from Harvard University and 0.7 miles from Brattle T...
  • Parking

No reviews yet 1 Reviews 1.0

from $91.00 Show details »

Forever Green Manor - 6 bedroom - Stunning Ocean Views in Winthrop, USA

Forever Green Manor - 6 bedroom - Stunni...

Holiday home in Winthrop near Chelsea, Massachusetts , 90 Highland Avenue
Forever Green Manor - 6 bedroom - Stunning Ocean Views offers accommodations in Winthrop, a 8-minute walk from Short Beach and 1.5 miles from Donovan ...
  • Parking
  • Family rooms

Exceptional 4 Reviews 9.7

from $1.726.66 Show details »

3 BR with parking near Downtown Boston in Somerville, USA

3 BR with parking near Downtown Boston

Holiday home in Somerville near Chelsea, Massachusetts , 15 Maine Terrace 2 Floor
3 BR with parking near Downtown Boston is a recently renovated vacation home in Somerville, near Cambridge College.
  • Parking
  • Pets allowed
  • Family rooms

Superb 9 Reviews 9.3

from $254.44 Show details »

Huge 1 Bed, 2 Baths, Harvard, Porter Davis Sq in Cambridge, USA

Huge 1 Bed, 2 Baths, Harvard, Porter Dav...

Holiday home in Cambridge near Chelsea, Massachusetts , 29 Montgomery Street
Huge 1 Bed, 2 Baths, Harvard, Porter Davis Sq is located in Cambridge, just 2.6 miles from Harvard Square and 2.6 miles from Inman Square.
  • Parking
  • Pets allowed

no reviews

from $303.99 Show details »

Pet-Friendly Revere Getaway, Steps from the T! in Revere, USA

Pet-Friendly Revere Getaway, Steps from...

Holiday home in Revere near Chelsea, Massachusetts
Pet-Friendly Revere Getaway, Steps from the T! is located in Revere, just 5.5 miles from Freedom Trail and 5.6 miles from Boston North Station.
  • Parking
  • Pets allowed

Very good 1 Reviews 8.0

from $241.64 Show details »

Revere Home Getaway in Revere, USA

Revere Home Getaway

Holiday home in Revere near Chelsea, Massachusetts , 20 Curtis Road
Revere Home Getaway is located in Revere, just a 8-minute walk from Revere Beach and 1.3 miles from Short Beach.
  • Parking
  • Pets allowed

no reviews

from $63.00 Show details »

CityScape in Chelsea, USA

CityScape

Holiday home in Chelsea, Massachusetts , 11 Lash St
CityScape is located in Chelsea, just 3.9 miles from Boston North Station and 3.9 miles from TD Garden.
  • Parking

no reviews

from $375.96 Show details »

Mystic River Escape Home Gym Office Near Encore in Medford, USA

Mystic River Escape Home Gym Office Near...

Holiday home in Medford near Chelsea, Massachusetts
Mystic River Escape Home Gym Office Near Encore is located in Medford, just 2.2 miles from Cambridge College and 3 miles from Inman Square.
  • Parking

no reviews

from $94.00 Show details »

In-between the Coast and the City in Everett, USA

In-between the Coast and the City

Holiday home in Everett near Chelsea, Massachusetts
In-between the Coast and the City is located in Everett, just 2.6 miles from Cambridge College and 3.9 miles from Freedom Trail.
  • Parking

Very good 4 Reviews 8.0

from $336.74 Show details »

Number of Holiday homes in Chelsea 31
Number of guest ratings 3,720
Average price per night $288.00
Lowest price per night $53,00
Highest price per night $1.087,75

Top 10 Cheapest Holiday-homes in Chelsea

Discover the Cheapest Holiday-homes in Chelsea – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Chelsea

Check out the Most Booked Holiday-homes in Chelsea – Based on Guest Popularity.

Holiday homes in Chelsea (Massachusetts), comfortable and familiar

Staying in a holiday or vacation home in Chelsea can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Chelsea for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Chelsea should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com