
Vacation rentals with breakfast in Gloucester
Find and book unique accommodations with breakfast on Airbnb
Quick stats about vacation rentals with breakfast included in Gloucester

Total vacation rentals
Explore 20 vacation rentals in Gloucester

Nightly prices starting at
Gloucester vacation rentals start at $154 CAD per night before taxes and fees

Verified guest reviews
Over 1,880 verified reviews to help you choose

Wifi availability
20 of Gloucester vacation 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 accommodations with breakfast in Gloucester
Guests agree: these breakfast rentals are highly rated for location, cleanliness, and more.

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, 193 reviews
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, 899 reviews
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, 229 reviews
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, 385 reviews
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, 506 reviews
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, 196 reviews
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, 434 reviews
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, 307 reviews
Stay safe in the heart of Beacon Hill in Boston.
This is true Beacon Hill. Right next to iconic Acorn street! Cozy, clean, quiet apartment. This spacious 1 bedroom apartment includes a comfortable queen bed , 1 full bath room, a sofa, a large flatscreen TV, and high-speed wifi. The kitchen is fully equipped with everything to cook simple meals, included coffee maker, microwave, pots/pans and toaster etc... Location is unbeatable, walking distance to the T, the Boston Commons, restaurants, city tours, night life, and more!
4.95 out of 5 average rating, 190 reviews
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!
4.89 out of 5 average rating, 219 reviews
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
4.96 out of 5 average rating, 46 reviews
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 reviewsPopular amenities for Gloucester accommodations with breakfast
House rentals with breakfast

Charming Cottage in Portsmouth Historic Waterfront
4.95 out of 5 average rating, 39 reviews
Conom Point, Essex, MA.

Centrally located 2 BR home

Captain Bayley House Captain's Quarters
5.0 out of 5 average rating, 415 reviews
The Seaside Suite- with views of Salem Commons
4.86 out of 5 average rating, 386 reviews
219 on the Ocean with Private Bath
4.96 out of 5 average rating, 494 reviews
North Shore Coastal Community/Post & Beam
4.91 out of 5 average rating, 510 reviews
Arlington Craftsman Green Room, Int. Well Restored
4.94 out of 5 average rating, 361 reviewsApartment rentals with breakfast

Private studio close to Boston and Harvard square
4.87 out of 5 average rating, 477 reviews
Charmer 2 bdr near the beaches
4.79 out of 5 average rating, 33 reviews
Spacious & Beautiful Entire Apt in Boston
4.99 out of 5 average rating, 67 reviews
Back-Bay Central Condo w Roof top, Gym & Parking
4.89 out of 5 average rating, 54 reviews
4BR.Wollaston Beach/15min Boston/Nice/Safe3b
5.0 out of 5 average rating, 58 reviews
Ocean and Woods! Best of both in Gloucester!
5.0 out of 5 average rating, 39 reviews
My Favorite Boston place
4.65 out of 5 average rating, 20 reviews
Bedroom w shared kitchen, bathroom & living room
4.85 out of 5 average rating, 234 reviewsBed and breakfast rentals with breakfast

Bright and sunny 1 bed with adjacent lounge area
4.93 out of 5 average rating, 165 reviews
Private living/dining/ kitchenette - Treetop Suite
5.0 out of 5 average rating, 126 reviewsA Room at the Top-sep. entrance, private bath
4.84 out of 5 average rating, 216 reviews
Peter • Best of Boston
4.92 out of 5 average rating, 1045 reviews
Historic relaxing clean home for 1- 2 adults
4.9 out of 5 average rating, 145 reviews
Crow's Nest Suite in Stylish Boutique Hotel
5.0 out of 5 average rating, 12 reviews
17th-Century Inn, Historic Salem Near Waterfront
4.97 out of 5 average rating, 65 reviews
Clark Currier Inn - Hale Room (3rd floor)
4.9 out of 5 average rating, 10 reviewsDestinations to explore
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