Vacation Rentals in Calderwood Pavilion, MA: Compare 10+ Sites & Save

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  4.  Massachusetts

  5.  Boston
  6.  Calderwood Pavilion

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2400 Best Vacation Rentals in Calderwood Pavilion (Starting from $66)

The Upton
The Upton
Apartment
Calderwood Pavilion, Boston, Massachusetts, USA
0.2k from Calderwood Pavilion center

Air Conditioner, Breakfast, Internet

7 Bedrooms15 Guests
6.5

Good

13 reviews

$129
Average price / night
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ASTONISHING 1 BEDROOM PARLOR, WELL APPOINTED, -SOUTH END BOSTON -BEST LOCATION
ASTONISHING 1 BEDROOM PARLOR, WELL APPOINTED, -SOUTH END BOSTON -BEST LOCATION
Apartment
Boston, MA, 02118, United States
0.1k from Calderwood Pavilion center

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

1 Bedroom2 Guests
10.0

Exceptional

52 reviews

$649
Average price / night
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Lower Level Studios In Hip Bay Village
Lower Level Studios In Hip Bay Village
Apartment
Boston, MA, USA
0.4k from Calderwood Pavilion center

Security/Safety, Air Conditioner, Internet, Fireplace/Heating, Child Friendly

3 Bedrooms2 Guests
7.1

Good

15 reviews

$335
Average price / night
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NEW Ultra-Luxury 4 bedroom Boston Designer Brownstone
NEW Ultra-Luxury 4 bedroom Boston Designer Brownstone
House
Boston, MA, 02116, United States
0.2k from Calderwood Pavilion center

AC, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms10 Guests
New to Booking
$1903
Average price / night
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Premier Suites Bay Village
Premier Suites Bay Village
Apartment
Boston, MA, USA
0.4k from Calderwood Pavilion center

Apartments, Accommodations, Serviced apartments, Lodgings, Places to stay

13 Bedrooms28 Guests
6.5

Good

17 reviews

$198
Average price / night
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Charming 1 BR apartment in Historic Bay Village
Charming 1 BR apartment in Historic Bay Village
Apartment
Boston, MA, 02116, United States
0.3k from Calderwood Pavilion center

AC, Heater, Internet, Living Area, No Smoking

1 Bedroom4 Guests
New to Booking
$275
Average price / night
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Centrally located Stay In Boston's Bay
Centrally located Stay In Boston's Bay
Apartment
Boston, MA, USA
0.4k from Calderwood Pavilion center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom2 Guests
4.8

Review score

17 reviews

$233
Average price / night
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Chic South End Studio With Patio
Chic South End Studio With Patio
Apartment
Boston, MA, 02116, United States
0.3k from Calderwood Pavilion center

AC, Barbecue, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom2 Guests
10.0

Exceptional

103 reviews

$398
Average price / night
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Enjoy Boston Private Patio On Montgomery Park
Enjoy Boston Private Patio On Montgomery Park
House
Boston, MA, USA
0.4k from Calderwood Pavilion center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
8.0

Good

1 reviews

$792
Average price / night
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* NEW Listing * A True GEM in South End , Boston!!
* NEW Listing * A True GEM in South End , Boston!!
House
Boston, MA, 02118, United States
0.3k from Calderwood Pavilion center

AC, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space, TV

1 Bedroom4 Guests
9.8

Exceptional

51 reviews

$585
Average price / night
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Global Luxury Suites in South End
Global Luxury Suites in South End
Apartment
Calderwood Pavilion, Boston, Massachusetts, USA
0.4k from Calderwood Pavilion center

Apartments, Luxury, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay

40 Bedrooms9 Guests
New to Booking
$234
Average price / night
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Private Studio In Boston's Bay Village!
Private Studio In Boston's Bay Village!
Apartment
Boston, MA, 02116, United States
0.4k from Calderwood Pavilion center

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

1 Bedroom2 Guests
6.0

Review score

4 reviews

$281
Average price / night
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Harmony Medical Suites on Canal
Harmony Medical Suites on Canal
Apartment
Calderwood Pavilion, Boston, Massachusetts, USA
0.4k from Calderwood Pavilion center

Internet, Pool, Air Conditioner, Balcony/Terrace, Kitchen, Pet Friendly, Wheelchair Accessible

4 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$210
Average price / night
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Affordable & Simple Chic Studio
Affordable & Simple Chic Studio
Apartment
Boston, MA, 02116, United States
0.4k from Calderwood Pavilion center

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

1 Bedroom2 Guests
7.6

Good

4 reviews

$281
Average price / night
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South End Studio Perfect for Work Travel #26
South End Studio Perfect for Work Travel #26
Apartment
Boston, MA, USA
0.4k from Calderwood Pavilion center

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

1 Bedroom1 Guest
7.7

Good

3 reviews

$66
Average price / night
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Furnished Studio in Downtown Boston #35
Furnished Studio in Downtown Boston #35
Apartment
Boston, MA, USA
0.4k from Calderwood Pavilion center

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

1 Bedroom2 Guests
7.0

Good

11 reviews

$245
Average price / night
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Luxury King Apartment - 2 Bedroom, Amazing Views - South End Boston
Luxury King Apartment - 2 Bedroom, Amazing Views - South End Boston
Apartment
Boston, MA, 02118, United States
0.4k from Calderwood Pavilion center

AC, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms8 Guests
3.4

Review score

3 reviews

$716
Average price / night
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Stylish 2 Bedroom in South End
Stylish 2 Bedroom in South End
Apartment
Boston, MA, USA
0.4k from Calderwood Pavilion center

Laundry, Internet, Balcony/Terrace

2 Bedrooms5 Guests
7.2

Good

35 reviews

$93
Average price / night
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Iconic & Luxurious Historic Townhouse with Roof Deck - A South End Gem 4BR & 3BA
Iconic & Luxurious Historic Townhouse with Roof Deck - A South End Gem 4BR & 3BA
House
Boston, MA, 02118, United States
0.4k from Calderwood Pavilion center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Laundry

4 Bedrooms8 Guests
New to Booking
$747
Average price / night
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Cozy Studio in Downtown Boston, #46
Cozy Studio in Downtown Boston, #46
Apartment
Boston, MA, USA
0.4k from Calderwood Pavilion center

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

1 Bedroom2 Guests
7.4

Good

8 reviews

$334
Average price / night
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Modern 1BRs steps from Boston Common + South End
Modern 1BRs steps from Boston Common + South End
Apartment
Boston, MA, 02116, United States
0.4k from Calderwood Pavilion center

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

1 Bedroom2 Guests
New to Booking
$551
Average price / night
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Downtown Boston Studio, #36
Downtown Boston Studio, #36
Apartment
Boston, MA, USA
0.4k from Calderwood Pavilion center

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

1 Bedroom2 Guests
8.5

Very Good

24 reviews

$334
Average price / night
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Modern Boston 2BR Apt. | Prime Downtown Location
Modern Boston 2BR Apt. | Prime Downtown Location
Apartment
Boston, MA, 02118, United States
0.4k from Calderwood Pavilion center

AC, Internet, Kitchen, Living Area, Pool, TV, Washer

2 Bedrooms4 Guests
New to Booking
$1046
Average price / night
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Modern, Smart 1Bed -Private Entry. Boston's Best Location Close to Everything
Modern, Smart 1Bed -Private Entry. Boston's Best Location Close to Everything
Apartment
Boston, MA, 02118, United States
0.4k from Calderwood Pavilion center

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

1 Bedroom2 Guests
New to Booking
$222
Average price / night
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One Such Boston Gem w Pvt Garden
One Such Boston Gem w Pvt Garden
Apartment
Boston, MA, 02116, United States
0.4k from Calderwood Pavilion center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
9.4

Superb

21 reviews

$653
Average price / night
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Cozy, Adorable 1-bedroom apartment - in tourist area.  Sleeps 4
Cozy, Adorable 1-bedroom apartment - in tourist area. Sleeps 4
Apartment
Boston, MA, 02116, United States
0.4k from Calderwood Pavilion center

AC, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

1 Bedroom4 Guests
9.8

Exceptional

58 reviews

$428
Average price / night
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Maverick Suites at 400 Columbus Ave
Maverick Suites at 400 Columbus Ave
Apartment
400 Columbus Ave, Boston, MA, 02116, United States
0.4k from Calderwood Pavilion center

Internet, Laundry, Microwave, No Smoking, TV

1 Bedroom2 Guests
7.4

Good

136 reviews

$233
Average price / night
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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 Calderwood Pavilion.

Where to stay in Calderwood Pavilion? Best neighborhoods & areas

Calderwood Pavilion Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2400 verified vacation rentals in Calderwood Pavilion. 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 Calderwood Pavilion vary depending on the season, property size, and location. Rates typically start from around $66 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 Calderwood Pavilion 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 Calderwood Pavilion welcome pets. Currently, 33 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 Calderwood Pavilion often include amenities such as Fireplace/Heating, Laundry, and Internet. 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.