Short-Term Rentals in Dogtown, MA: Compare 10+ Sites & Save

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  5.  Gloucester
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390 Best Short-Term Rentals in Dogtown (Starting from $129)

Waterfront Escape Dock & More
Waterfront Escape Dock & More
House
Gloucester, MA, USA
1.9k from Dogtown center

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

4 Bedrooms12 Guests
New to Booking
$1025
Average price / night
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River Watch: Waterfront home with river views and a private dock.
River Watch: Waterfront home with river views and a private dock.
House
Gloucester, MA, 01930, United States
1.4k from Dogtown center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
9.4

Superb

9 reviews

$886
Average price / night
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OFFICIAL SITE - Buoy 23 Vacation Home Gloucester, MA Deepwater dock
OFFICIAL SITE - Buoy 23 Vacation Home Gloucester, MA Deepwater dock
House
Gloucester, MA, USA
1.9k from Dogtown center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms7 Guests
New to Booking
$615
Average price / night
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Sunset Views, Waterfront Property, Dock - Sleeps 12
Sunset Views, Waterfront Property, Dock - Sleeps 12
House
Gloucester, MA, 01930, United States
1.5k from Dogtown center

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

4 Bedrooms12 Guests
10.0

Exceptional

97 reviews

$450
Average price / night
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Bianca's House
Bianca's House
House
Gloucester, MA, USA
2.3k from Dogtown center

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

2 Bedrooms4 Guests
6.0

Review score

3 reviews

$326
Average price / night
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Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam
Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam
House
Gloucester, MA, 01930, United States
1.6k from Dogtown center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$515
Average price / night
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Spacious 2nd floor Suite
Spacious 2nd floor Suite
Apartment
Gloucester, MA, USA
2.4k from Dogtown center

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

2 Bedrooms4 Guests
7.1

Good

7 reviews

$173
Average price / night
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Evensong: Oceanview Retreat with Dock
Evensong: Oceanview Retreat with Dock
House
Gloucester, MA, 01930, United States
1.6k from Dogtown center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

3 Bedrooms8 Guests
10.0

Exceptional

50 reviews

$594
Average price / night
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Glorious Suite near Downtown with washer/dryer
Glorious Suite near Downtown with washer/dryer
Apartment
Gloucester, MA, USA
2.4k from Dogtown center

Parking, Internet, Security/Safety, Child Friendly

3 Bedrooms4 Guests
8.7

Fabulous

19 reviews

$291
Average price / night
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Amazing Waterfront/Access 4BDRM in Riggs Point
Amazing Waterfront/Access 4BDRM in Riggs Point
Cottage
Gloucester, MA, 01930, United States
1.6k from Dogtown center

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

4 Bedrooms8 Guests
9.2

Superb

15 reviews

$504
Average price / night
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Massachusetts Abode with Deck and Grill Near Beaches!
Massachusetts Abode with Deck and Grill Near Beaches!
House
Gloucester, MA, USA
2.4k from Dogtown center

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

2 Bedrooms4 Guests
9.3

Superb

4 reviews

$425
Average price / night
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Mill Pond Cottage: Timeless Gloucester Elegance
Mill Pond Cottage: Timeless Gloucester Elegance
House
Gloucester, MA, 01930, United States
1.6k from Dogtown center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$553
Average price / night
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Guest suite in historical district
Guest suite in historical district
Apartment
Gloucester, MA, USA
2.7k from Dogtown center

Parking, Air Conditioner, Security/Safety, Guest Services, Internet, Sports/Activities, Breakfast

2 Bedrooms4 Guests
9.1

Superb

43 reviews

$180
Average price / night
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Sunset Cove: Waterfront at Goose Cove
Sunset Cove: Waterfront at Goose Cove
House
Gloucester, MA, 01930, United States
1.7k from Dogtown center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
8.8

Fabulous

22 reviews

$771
Average price / night
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Walk To Good Harbor OCEAN VIEWS Open All Year
Walk To Good Harbor OCEAN VIEWS Open All Year
House
Gloucester, MA, USA
2.7k from Dogtown center

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

3 Bedrooms6 Guests
New to Booking
$803
Average price / night
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Oceanfront Dock Escape ~ Kayaks & Paddleboards
Oceanfront Dock Escape ~ Kayaks & Paddleboards
House
Gloucester, MA, 01930, United States
1.9k from Dogtown center

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

4 Bedrooms10 Guests
10.0

Exceptional

5 reviews

$910
Average price / night
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Gloucester Harbor Hideaway
Gloucester Harbor Hideaway
Apartment
Gloucester, MA, USA
2.7k from Dogtown center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

2 Bedrooms4 Guests
9.4

Superb

5 reviews

$402
Average price / night
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Thurston Point: Deepwater River Dock
Thurston Point: Deepwater River Dock
House
Gloucester, MA, 01930, United States
1.9k from Dogtown center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms7 Guests
9.4

Superb

22 reviews

$762
Average price / night
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Longview House
Longview House
House
Gloucester, MA, USA
2.8k from Dogtown center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family, Accessible hotels

4 Bedrooms9 Guests
6.0

Review score

2 reviews

$383
Average price / night
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Annisquam Singing Pines: Riverfront Splendor
Annisquam Singing Pines: Riverfront Splendor
House
Gloucester, MA, 01930, United States
1.9k from Dogtown center

AC, Barbecue, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
9.0

Fabulous

13 reviews

$1223
Average price / night
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Ocean Breeze-8min Walk to Beach
Ocean Breeze-8min Walk to Beach
Apartment
Gloucester, MA, USA
2.8k from Dogtown center

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

1 Bedroom4 Guests
9.6

Exceptional

32 reviews

$249
Average price / night
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Waterfront Home with Spectacular Viewsof the Annisquam River
Waterfront Home with Spectacular Viewsof the Annisquam River
House
Gloucester, MA, 01930, United States
2.0k from Dogtown center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

6 Bedrooms10 Guests
9.8

Exceptional

69 reviews

$654
Average price / night
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Clean Waterfront Classic Cottage with Private Beach
Clean Waterfront Classic Cottage with Private Beach
House
Gloucester, MA, 01930, United States
2.0k from Dogtown center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms7 Guests
9.8

Exceptional

25 reviews

$402
Average price / night
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Downtown Dahlias fully remodeled in the heart of Gloucester
Downtown Dahlias fully remodeled in the heart of Gloucester
House
Gloucester, MA, 01930, United States
2.1k from Dogtown center

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

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$482
Average price / night
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Cozy two bedroom house in the heart of Gloucester
Cozy two bedroom house in the heart of Gloucester
House
Gloucester, MA, 01930, United States
2.2k from Dogtown center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.4

Superb

14 reviews

$260
Average price / night
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Cozy Apartment at Green Landing - AC - No Cleaning Fee - Hassle Free Check Out
Cozy Apartment at Green Landing - AC - No Cleaning Fee - Hassle Free Check Out
Apartment
Gloucester, MA, 01930, United States
2.2k from Dogtown center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
New to Booking
$276
Average price / night
Check Availability
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
Apartment
Gloucester, MA, 01930, United States
2.2k from Dogtown center

Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, Outdoor Space

1 Bedroom2 Guests
9.6

Exceptional

51 reviews

$129
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 Short-Term Rentals in Dogtown.

Dogtown Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 390 verified short-term rentals in Dogtown, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Dogtown vary depending on location, property size, and travel dates. Rates typically start from around $129 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Dogtown include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Dogtown, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Dogtown often include amenities such as Fireplace/Heating, Kitchen, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Dogtown are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.