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Holiday rentals with breakfast in Gloucester

Find and book unique rentals with breakfast on Airbnb

Quick stats about holiday rentals with breakfast included in Gloucester

  • Total holiday rentals

    Explore 20 holiday rentals in Gloucester

  • Nightly prices starting at

    Gloucester holiday rentals start at €95 per night before taxes and fees

  • Verified guest reviews

    Over 1,880 verified reviews to help you choose

  • Wifi availability

    20 of Gloucester holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Gloucester rentals

  • 4.9 Average rating

    Gloucester stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated rentals with breakfast in Gloucester

Guests agree: these breakfast rentals are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of the historic John Brewer house is shown, featuring a red wooden façade with multiple windows and flower boxes. An American flag is displayed prominently, and decorative elements like corn husks and seasonal flowers enhance the welcoming appearance. Sidewalks and roadways are visible in the foreground.
Flat in Ipswich

Charming 2 Bedroom Apartment in Historic Ipswich.

In the heart of historic downtown Ipswich, the John Brewer house has been a family home since 1680! This fully renovated apartment features many modern amenities, like hi-speed internet, 50" and 55" televisions with streaming channels. There is parking for two cars, and we are a short walk to Market Street, the commuter rail to Boston, a large park for children, and many fantastic local restaurants. Drive to Boston or Maine in 45 mins; Salem or Gloucester in 30 mins; Crane Beach in 10 mins!

4.98 out of 5 average rating, 190 reviews
Top guest favourite
The historic brick facade of a Greek Revival home is adorned with blue shutters and a welcoming navy front door. Red, white, and blue bunting is displayed around the entrance, complemented by lush planters on either side. A large American flag is hoisted above, enhancing the patriotic charm.
Guest suite in Downtown Salem

The Mason Suite of Salem

*We have THE BEST location in all of Salem! Take a look at our reviews!* The Mason Suite is a boutique lodging experience with all the comforts of home! Built in 1844 and nestled among Salem's most prized architecture, the Suite is just steps from the Witch Museum, bustle of the pedestrian mall, and Salem Common! Recently renovated from top to bottom! You'll be surrounded by fine furnishings, culture and history! The location is 10/10! We strive to provide you with the ideal Salem experience!

4.99 out of 5 average rating, 892 reviews
Top guest favourite
The image features a serene marina scene under a clear blue sky, with various boats docked along the water. Towering trees and greenery frame the view, while the gentle architecture of nearby buildings adds to the coastal landscape.
Home in Gloucester

Rocky Neck Retreat

.Relaxing private location .4 beds 2 baths with full kitchen/pans/Dishwasher/Wash/Dryer.Renovated organic design integrates historic architecture with modern touches.If you come for hikes, beach/music/food scene, you will enjoy the Rocky Neck District .The unique home has 4 bedrooms /4 Queen Beds. Speedy WIFI .Parking is up a steep narrow drive . NO trucks or XL SUVs. 2 cars max. Note* Kitchen and LR are upstairs.There are stairs. Contact owner for questions re:parking or limited mobility.

4.99 out of 5 average rating, 228 reviews
Top guest favourite
A cozy living room is highlighted by wood paneling and exposed beams. Plush seating includes a sofa and two armchairs. A coffee table is centered in the space, with a television displaying programming. Natural light fills the room through multiple windows adorned with soft curtains.
Home in Brighton

All the comforts of home, quiet city neighborhood

Sleep peacefully in this beautiful home above Oak Square>Brighton>Boston. Updated, comfortably furnished, well-stocked with electronics, appliances, and housewares. Driveway parking spot. Ideal for couples, solo adventurers, and business travelers with auto or use ride services. Laundry service one mile away. Newbury Street: 8 miles away, North End: 9 miles, Seaport: 9 miles, Logan airport: 11 miles. Close to BC/Harvard; 1 mile from I-90/Mass Pike in Newton Corner, restaurants, attractions.

4.93 out of 5 average rating, 380 reviews
Top guest favourite
The exterior of the private studio is shown, featuring a light blue siding with a gray shingled roof. A welcoming front door is flanked by a light fixture and a decorative sign. Flowering plants are arranged in front, enhancing the outdoor space.
Cottage in Winthrop

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

4.98 out of 5 average rating, 504 reviews
Guest favourite
A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.
Home in Salem

Quaint Little New Hampshire Lake House Getaway!

Imagine the peace and quiet of looking out a wall of glass seeing the tranquility of the lake while knowing 10 minutes away is shopping, restaurants entertainment and just about anything you could ask for to meet your needs. 10 minutes from the highway, 35 minutes from Boston, 35 minutes from the ocean and 1 1/2 hours from the mountains. We are a central point to anything you’re looking for. Newly renovated lake house with all the up to date amenities. Come and enjoy a night or week.

4.94 out of 5 average rating, 194 reviews
Top guest favourite
The living room is defined by vibrant purple walls and rich hardwood flooring. A large light blue sofa is accompanied by a red armchair and a central round table draped in a deep purple cloth. Colorful textiles and decorative accents add charm to the space.
Flat in Salem

The Creaky Cauldron-Wizards and Witches Welcome!

Welcome to The Creaky Cauldron, an enchanting escape inspired by the world of witches and wizards located in the heart of Salem! We have put a lot of love into creating a special and unique experience for visitors to the Witch City who love magic and Salem as much as we do. Each room has been carefully themed after a magical house or subject to give our guests an immersive experience. Each of our 7 rooms is inspired by each of the 7 books in our favorite magical fantasy series.

4.96 out of 5 average rating, 426 reviews
Top guest favourite
A vibrant bedroom is presented, featuring a gold sun mural on a purple wall. An ornate headboard supports a spacious bed adorned with an orange and colorful patterned blanket. Decorative artwork and artifacts add character, while a unique lamp provides soft lighting.
Flat in Salem

The Ghoul’s Attic-For 90s Witches and Wannabes

No ghoulies or ghosties here--just a unique and magical escape inspired by everyone's favorite school of magic--located upstairs at The Creaky Cauldron B&B in the heart of Salem! We have put a lot of love into creating a special and unique experience for visitors to the Witch City who love magic and Salem as much as we do. Each room has been carefully themed after a magical house and/or subject to give our guests an immersive experience in the world of witchcraft and wizardry.

4.96 out of 5 average rating, 301 reviews
Superhost
Home in Malden

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free

Stay in our elegant Boho-Modern Home Only 15min from Boston's Major Attractions. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dinning and Large Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Laundry Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

4.9 out of 5 average rating, 216 reviews
Top guest favourite
Home in Beverly

Villaggio By The Sea.

Peaceful hillside retreat on the North Shore offering scenic views and relaxing, escape, spectacular living room, fully equipped kitchen and dining area perfect for gathering features for large bedrooms, one king 2 queen 2 twin and three full bathrooms, enjoy patios, outdoors, entertaining, and a quiet deck, ideal for family, vacation, weddings, and special occasions, near beaches, dining, and historic coastal towns .On site property has a lower-level apartment

4.98 out of 5 average rating, 44 reviews
Top guest favourite
Flat in Newmarket

Spacious private Studio & Experienced SuperHosts!

Move-in ready, furnished & fully equipped apartment near downtown & river in working class, generally quiet pocket neighborhood. Separate entrance, spacious sleeping/living room, lots of windows, DOUBLE bed, couch, AC, TV, cable & WiFi, 3/4 bath. We disinfect spaces with UVC lamp & hospital-grade cleaning products as part of our deep cleaning & disinfection protocols. WALK to local fresh market, restaurants, cafes & bars for takeout or eat in.

4.97 out of 5 average rating, 264 reviews
Guest favourite
Flat in Dorchester

Apartment 1BR mins from JFK/UMASS free parking

Airbnb Superhost offering meticulous and spacious 1 bedroom 1 bath, queen bed plus sleep sofa and airbed (please request it when booking). Free street parking or in the driveway, free laundry, full kitchen, hardwood and tile floors. Wireless internet, smart TV. 10 min walk to Red Line JFK/UMass station and Savin Hill station. Free parking on the street or in our driveway. Well kept front yard and back yard with porch, chairs and table.

4.93 out of 5 average rating, 483 reviews

Popular amenities for rentals with breakfast in Gloucester

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with breakfast

Top guest favourite
Home in Portsmouth

Charming Cottage in Portsmouth Historic Waterfront

4.94 out of 5 average rating, 35 reviewsThe exterior of a blue Victorian home is captured, displaying a wraparound porch adorned with flowers. An American flag is mounted by the entrance. The property is framed by a lush green lawn and is situated near a peaceful bay, with a road leading up to the house.
Home in Essex

Conomo Point, Essex, MA.

Home in Salem

Centrally located 2 BR home

Top guest favourite
The guest suite features a queen canopy bed adorned with decorative pillows, complemented by a roll-out youth-sized trundle bed. A wooden dresser sits beside the bed, and light enters through a partially closed window, illuminating the room's soft blue walls.
Private room in Newburyport

Captain Bayley House Captain's Quarters

5.0 out of 5 average rating, 409 reviews
Top guest favourite
A historic building with a dark blue exterior showcases multiple windows framed by greenery and vibrant purple doors. A well-maintained lawn extends in front, while a vehicle is parked in the driveway, providing a welcoming view of the property.
Private room in Salem

The Seaside Suite- with views of Salem Commons

4.86 out of 5 average rating, 384 reviews
Top guest favourite
Private room in Dorchester

Savin Hill by the Sea with Private Bath

4.97 out of 5 average rating, 460 reviews
Guest favourite
The exterior of a two-story gray house is surrounded by lush greenery and well-maintained landscaping. Large windows reflect natural light, while a spacious wooden deck enhances outdoor access. Nearby trees and a clear sky provide a serene backdrop, contributing to the tranquil rural setting.
Private room in Rowley

North Shore Coastal Community/Post & Beam

4.91 out of 5 average rating, 510 reviews
Top guest favourite
A large furnished room features a wooden wardrobe and a vintage chest of drawers. A small desk with a lamp is positioned beside a red accent chair. Light blue walls and a carpet add a cozy feel, complemented by decorative wall trim.
Private room in Winthrop

Winthrop Home With A View

4.91 out of 5 average rating, 109 reviews

Apartment rentals with breakfast

Superhost
A comfortable sleeping area features a spacious bed dressed in white bedding, complemented by decorative pillows. A colorful floral wall art piece adds a pop of color above the bed. Natural light enters through a nearby window, illuminating the hardwood floor.
Flat in Watertown

Private studio close to Boston and Harvard square

4.87 out of 5 average rating, 472 reviews
Guest favourite
The living room features a comfortable gray sofa adorned with decorative cushions, accompanied by a wooden coffee table. Natural light filters through large bay windows, enhancing the cozy ambiance. Wall-mounted decorative plates and a small table with potted plants add character to the space.
Flat in Lynn

Charmer 2 bdr near the beaches

4.77 out of 5 average rating, 30 reviews
Top guest favourite
The image captures a broad, paved walkway along a beach, with views of the ocean in the background. Several benches are positioned under wooden canopies, providing shade for visitors. People are seen walking leisurely, enjoying the peaceful coastal atmosphere.
Flat in Quincy

4BR.Wollaston Beach/15min Boston/Nice/Safe3b

5.0 out of 5 average rating, 57 reviews
Guest favourite
A modern living room features a plush gray sofa with decorative cushions and a wooden coffee table. A large flat-screen TV is mounted on the wall, and large windows provide ample natural light, offering a view of the cityscape. A doorway leads to a bedroom space.
Flat in Kendall Square

Back-Bay Central Condo w Roof top, Gym & Parking

4.88 out of 5 average rating, 51 reviews
Guest favourite
A living area features a blue sofa with two dark green cushions, positioned in front of a multi-colored area rug. A small dark wood side table with a lamp is nearby, and a dining area is visible in the background with a red wall and a table set for dining.
Flat in Dorchester

Spacious & Beautiful Entire Apt in Boston

4.99 out of 5 average rating, 67 reviews
Guest favourite
A charming two-story home features a stone chimney and a variety of flowering plants in the garden. The exterior showcases a mix of wood and stone, with large windows allowing natural light to fill the interior. Green grass surrounds the property, complemented by trees.
Flat in Gloucester

Ocean and Woods! Best of both in Gloucester!

5.0 out of 5 average rating, 39 reviewsA spacious kitchen is equipped with wooden cabinetry, a large dining table capable of seating six, and modern appliances. Natural light is provided through a window above the sink, while a warm glow is created by overhead lighting. The floor features textured tiles.
Flat in Medford

My Favorite Boston place

4.65 out of 5 average rating, 20 reviews
Top guest favourite
A cozy living area features a blend of comfortable seating, including a red armchair and a patterned couch. A wooden coffee table sits at the center, accompanied by a decorative rug. Natural light filters through the windows, enhancing the warm tones of the space.
Private room in Dorchester

Private room/ MUST LOVE DOGS

4.9 out of 5 average rating, 211 reviews

Bed and breakfast rentals with breakfast

Top guest favourite
A cozy sleeping area features soft bedding with decorative pillows against a dark wood headboard. Two bedside tables with lamps are positioned on either side. Fresh flowers are placed beside the bed, and stacked towels are arranged on a tray at the foot of the bed.
Private room in West Newbury

Bright and sunny 1 bed with adjacent lounge area

4.93 out of 5 average rating, 164 reviews
Top guest favourite
A well-lit queen bedroom features a plush bed with a decorative blanket and a soft throw. Two windows adorned with light curtains allow natural light to fill the room, while soft colors on the walls create a calming atmosphere. A framed art piece is visible on the wall.
Private room in Watertown

Private living/dining/ kitchenette - Treetop Suite

5.0 out of 5 average rating, 124 reviews
Guest favourite
A dining space is set with an assortment of dishes on a wooden table, surrounded by several chairs. Soft lighting illuminates the area, highlighting a cozy atmosphere. Shelves filled with books line the walls, while potted plants add a touch of greenery.
Private room in Somerville

Peter • Best of Boston

4.92 out of 5 average rating, 1038 reviews
Guest favourite
A bright living area is filled with natural light from skylights in the angled ceiling. A spacious bed with a light-colored coverlet is positioned centrally, complemented by a soft rug. Two comfortable sofas and a bookshelf add to the inviting ambiance.
Private room in Cambridge

A Room at the Top-sep. entrance, private bath

4.84 out of 5 average rating, 214 reviews
Top guest favourite
A cozy bedroom features a double bed with a patterned blanket and a light-colored bed skirt. Natural light floods the space through a skylight and a window with sheer curtains. A dresser and a round mirror complement the decor, while soft flooring adds warmth.
Private room in Cambridge

Smack dab between Harvard+Porter 2

4.98 out of 5 average rating, 330 reviews
Guest favourite
A spacious guest room features two full-size beds adorned with vibrant red and blue bedding. A day bed is positioned against the wall, complemented by an artwork depicting a historical scene. Large windows, draped with bright red curtains, allow natural light to illuminate the room.
Private room in Salem

17th-Century Inn, Historic Salem Near Waterfront

4.97 out of 5 average rating, 64 reviews
Superhost
A spacious bed is dressed in white linens, complemented by a textured wooden headboard. Neatly rolled towels are arranged on the bed, while a bedside table with a softly lit lamp adds functional elegance to the sleeping area.
Hotel room in Rockport

Crow's Nest Suite in Stylish Boutique Hotel

5.0 out of 5 average rating, 11 reviews
Guest favourite
A cozy entryway features two upholstered chairs and a wooden dresser against a light green wall. Natural light filters through a window adorned with shades. A door leads to the outside garden, while a potted plant adds a touch of greenery to the space.
Hotel room in Newburyport

Clark Currier Inn - Merrimac Room

4.86 out of 5 average rating, 22 reviews

Destinations to explore