Guesthouses in Gloucester You’ll Love

Top-Rated Gloucester Guesthouses for Every Budget and Style!

Looking for a guesthouse in Gloucester (Massachusetts)? Discover and compare a wide selection of cozy guesthouses, bed & breakfast and inns in Gloucester – perfect for solo travelers, couples, or families. Whether you’re planning a weekend getaway or an extended stay, you’ll find charming, affordable options starting at just $66.00 per night. From centrally located guesthouses near downtown to peaceful retreats close to the beach, explore accommodations that match your style and budget.

Easily browse photos, read guest reviews, and book the ideal guesthouse in Gloucester today.

We found 13 Guest-houses in Gloucester and the surrounding area (within 40 miles)

Eagle House Motel

Motel in Rockport near Gloucester, Massachusetts , 8 Cleaves Street

This Rockport motel is 1640 feet away from Bearskin Neck.

Parking

Fabulous 186 Reviews 8.9

from $161.97 Show details »

The Vista

Motel in Gloucester, Massachusetts , 22 Thatcher Road

Overlooking Good Harbor Beach in Gloucester, all rooms at the Vista Motel have ocean views.

Parking
Outdoor pool
Swimming pool
Swimming Pool

Fabulous 309 Reviews 9.0

from $168.44 Show details »

Sea Lion Motel

Motel in Gloucester, Massachusetts , 138 Eastern Avenue

Located 10 minutes’ walk from Good Harbor Beach, this motel features an outdoor pool and whale watching tours within 1 mile.

Parking
Family rooms
Outdoor pool
Swimming pool
Swimming Pool

Fabulous 221 Reviews 8.7

from $160.85 Show details »

Bearskin Neck Motor Lodge

Motel in Rockport near Gloucester, Massachusetts , 64 Bearskin Neck

This oceanfront motel in Rockport, Massachusetts features a spacious deck area with outdoor furniture.

Parking

Fabulous 78 Reviews 8.9

from $256.91 Show details »

Cape Ann Motor Inn

Motel in Gloucester, Massachusetts , 33 Rockport Road

Located on the Long Beach in Gloucester, this property offers rooms with views of the ocean.

Parking
Pets allowed

Fabulous 278 Reviews 9.0

from $178.04 Show details »

Sally Webster Inn

B&B in Rockport near Gloucester, Massachusetts , 34 Mount Pleasant St

Sally Webster Inn offers accommodations in Rockport, a 10-minute walk from Front Beach and 0.8 miles from Back Beach.

Parking

Fabulous 84 Reviews 8.6

from $226.75 Show details »

Seafarer Inn

B&B in Rockport near Gloucester, Massachusetts , 50 Marmion Way

Seafarer Inn enjoys a location in Rockport, 1.5 miles from Back Beach and 22 miles from Peabody Essex Museum.

Parking
Family rooms

Superb 75 Reviews 9.3

from $255.63 Show details »

Lantana House

B&B in Rockport near Gloucester, Massachusetts , 22 Broadway

Lantana House offers accommodations in Rockport, 20 miles from Peabody Essex Museum and 20 miles from The House of the Seven Gables.

Parking
Family rooms

Fabulous 53 Reviews 9.0

from $258.03 Show details »

Beach & King Street Inn

B&B in Rockport near Gloucester, Massachusetts , 2 King Street PO BOX 750

Beach & King Street Inn in Rockport provides adults-only accommodations with a garden and a terrace.

Parking
Allergy-free room

Exceptional 28 Reviews 9.7

from $346.55 Show details »

The Beech Tree B&B

B&B in Rockport near Gloucester, Massachusetts , 55 Broadway

The Beech Tree B&B in Rockport provides adults-only accommodations with a garden and a terrace.

Parking

Exceptional 15 Reviews 9.6

from $100.00 Show details »

Yankee Clipper Inn

Inn in Rockport near Gloucester, Massachusetts , 127 Granite Street

Overlooking the Atlantic Ocean, the Yankee Clipper Inn is a 1929 art deco mansion in the seaside town of Rockport, Massachusetts.

Parking
Outdoor pool
Kid-friendly buffet
Swimming pool
Swimming Pool

Fabulous 134 Reviews 8.7

from $222.39 Show details »

Harborview Inn

Inn in Gloucester, Massachusetts , 71 Western Avenue

Featuring a terrace, Harborview Inn is located in Gloucester in the Massachusetts region, a 5-minute walk from Pavilion Beach and 0.6 miles from Halfm...

Parking
Allergy-free room

Superb 100 Reviews 9.3

from $211.11 Show details »

Sheas Riverside Inn & Motel

Inn in Essex near Gloucester, Massachusetts , 132 Main Street

Located in Essex, within 12 miles of Peabody Essex Museum and 12 miles of The House of the Seven Gables, Sheas Riverside Inn & Motel provides accommod...

Parking

Superb 41 Reviews 9.1

from $229.27 Show details »

Number of Guesthouses in Gloucester	13
Number of guest ratings	2,121
Average price per night	$160.00
Lowest price per night	$66,00
Highest price per night	$290,28

Guesthouses in Gloucester (Massachusetts), small and cozy

Guesthouses are small, cozy accommodations that offer a more personal and authentic experience than larger hotels. Often family-owned and operated, guesthouses provide a home-away-from-home atmosphere for travelers seeking a warm and welcoming environment. Typically located in residential areas or rural settings, guesthouses offer a peaceful and relaxing escape from the hustle and bustle of the city. With a focus on personalized service and attention to detail, guests can expect comfortable rooms, authentic food, and insider tips on local attractions and activities. Whether you're looking for a romantic getaway, a family vacation, or a solo adventure, guesthouses in Gloucester offer a unique and memorable way to experience a new destination.

Find the best guesthouse in Gloucester for your needs

When looking for the best guesthouse for your next stay in Gloucester, there are a few key factors to consider. First and foremost, location is important - choose a guesthouse that is conveniently located to the attractions and activities that you want to experience. Next, read reviews from previous guests to get a sense of the guesthouse's quality, cleanliness, and hospitality. Look for guesthouses that have consistently positive reviews and a high rating. Additionally, consider the amenities offered, such as free Wi-Fi, breakfast, and on-site parking. Finally, don't forget to consider the price - guesthouses can vary widely in price, so be sure to choose one that fits within your budget. With these factors in mind, you can find the best guesthouse in Gloucester for your next vacation and enjoy a memorable and comfortable stay.

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Guesthouses in Gloucester You’ll Love

Top-Rated Gloucester Guesthouses for Every Budget and Style!

We found 13 Guest-houses in Gloucester and the surrounding area (within 40 miles)

Guesthouses in Gloucester (Massachusetts), small and cozy

Find the best guesthouse in Gloucester for your needs