Holiday rentals with breakfast in Gloucester

Find and book unique Holiday Accommodation with Breakfast on Airbnb

Top-rated Holiday Accommodation with Breakfast in Gloucester

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Guest favourite

Home in Gloucester

4.99 out of 5 average rating, 154 reviews

Rocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry

.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 Large SUVs. 2 cars max. Note* Kitchen and LR are upstairs.There are stairs. Contact owner for questions re:parking or limited mobility.

6 – 13 Dec

$6,879 AUD total

Guest favourite

Guest suite in Windham

4.99 out of 5 average rating, 243 reviews

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

26 Oct – 2 Nov

$1,679 AUD total

Guest favourite

Home in Windham

4.92 out of 5 average rating, 259 reviews

One Level 2 bedroom suite on private cul-de-sac

Welcome to The Sama's Airbnb. Windham was recently named the #1 town in the Granite State. Here, you will enjoy a complete newly renovated private one level 2 bedroom suite complete with full kitchen, cozy living room, 40 inch LED TV with all channels, wifi, washer and dryer, new tennis court, 1/2 basketball court and pickleball, beautifully landscaped grounds on a private cul de sac yet close to Boston, beaches, mountains, shopping, great restaurants, Searles Castle, Canobie, & Tuscan Village.

9 – 16 Feb

$1,902 AUD total

Guest favourite

Apartment in Ipswich

4.98 out of 5 average rating, 121 reviews

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!

6 – 13 Apr

$1,925 AUD total

Guest favourite

Apartment in Marblehead

4.93 out of 5 average rating, 155 reviews

Two bedroom Apt with a deck

2nd floor apt, located on Pleasant St, the main road into Historic downtown Marblehead. Cute deck, main entrance to apt is off the deck. The apt is only minutes walk from great restaurants, gym, yoga studio, bike /running trail. 15 min walk to the beach (4 min drive) and historic downtown and uptown where you will find tons of really great shops. The apt is tastefully decorated and is quiet.see house rules Dogs are very welcome, but need to be house trained + friendly with other dogs/people.

11 – 18 Nov

$1,830 AUD total

Guest favourite

Guest suite in Salem

4.99 out of 5 average rating, 693 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!

1 – 8 Jan

$2,367 AUD total

Guest favourite

Apartment in Beverly

5.0 out of 5 average rating, 49 reviews

West Street Retreat

Newly renovated, three bedroom apartment with spacious open concept in a charming New England home. Centrally located north of Boston in Beverly Farms, with easy access to the area's many beaches, historic sites, and quaint seaside towns which are full of restaurants, shops and galleries. Avoid the traffic into Boston. The train is only a block away. And the Retreat is only minutes from Endicott College, Gordon College, and Landmark which makes it ideal for families visiting those schools.

12 – 19 Oct

$4,606 AUD total

Guest favourite

Cottage in Rockport

5.0 out of 5 average rating, 11 reviews

Periwinkle Cottage #2 walk to everything you love!

In 2024 - we are honored to celebrate 15 years in business! A tranquil and serene space welcomes you with light colored walls and loads of natural light. This unit has everything you'll need for a short getaway or a longer stay. Walking distance to everything Rockport has to offer with full kitchen, parking, laundry (for stays 7-nights or longer only), gas grill, Wifi with all linens supplied and more. Located on a dead-end street both units are quiet and private. Book your stay today!1

21 – 28 Aug

$3,337 AUD total

Guest favourite

Apartment in Newmarket

4.96 out of 5 average rating, 198 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. We disinfect spaces with UVC lamp & hospital-grade cleaning products as part of our deep cleaning & disinfection protocols, often closing between guests. Distance check-in. WALK to local fresh market, restaurants, cafes & bars for takeout or eat in.

$145 AUD per night

Guest favourite

Place to stay in Salem

4.98 out of 5 average rating, 201 reviews

Seadrift Inn - 2 bedroom 2nd floor apt by the sea!

We are at Salem Willows - family-friendly activities, the ferry, trolley, train, downtown, and nightlife are all close by. Seadrift is perfect for couples traveling together as it has two bedrooms, both with King beds, a large living room, and bathroom. You have a private entrance and it is located on the second floor. You can walk to four beaches within minutes, one is right outside your door. Salem has many historic landmarks and wonderful restaurants very close by. Come visit!!

6 – 13 May

$2,716 AUD total

Guest favourite

Guest suite in Rockport

4.99 out of 5 average rating, 611 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

22 – 29 Apr

$1,633 AUD total

Superhost

Home in Beverly

4.84 out of 5 average rating, 146 reviews

Beverly Beach House- Upper Deck

Half block from the beach in the scenic North Shore. Get away from it all in this beach bungalow. Close to downtown restaurants and shops, Historic Cabot theater and more. Large historic colonial home with 3 bedrooms and 2 bath with ocean views and off street parking. Large deck and full kitchen. 30 min train to Boston. Easy quick access to popular destinations such as Marblehead, Rockport, Newburyport, Gloucester and more.

29 Nov – 6 Dec

$4,268 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Gloucester Holiday Accommodation with Breakfast

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with breakfast

Superhost

Home in Ipswich

4.83 out of 5 average rating, 58 reviews

Hillside Ocean View 2BR with Private Beach Access

18 – 25 Nov

$3,335 AUD total

Guest favourite

Home in Maynard

5.0 out of 5 average rating, 14 reviews

Cute mill house: 3BR•Wood stove *Brkfst included*

25 Aug – 1 Sept

$3,465 AUD total

Guest favourite

Home in Winthrop

5.0 out of 5 average rating, 25 reviews

Luxury 3BR/2BA Home Featured in Boston Magazine

6 – 13 Sept

$7,296 AUD total

Guest favourite

Home in Hampton

5.0 out of 5 average rating, 27 reviews

Contemporary Home-nr Beach/HotTub/Lg Stylish Patio

20 – 27 Sept

$8,454 AUD total

Home in Kittery

4.8 out of 5 average rating, 183 reviews

Charming Private New England Cape

11 – 18 Oct

$3,820 AUD total

Home in Gloucester

4.92 out of 5 average rating, 13 reviews

Good Harbor Beach Home - 1 min walk to Beach!

20 – 27 Feb

$10,670 AUD total

Guest favourite

Home in Newburyport

4.97 out of 5 average rating, 69 reviews

Plovers Nest: Romantic Fireplace Sunset Central AC

24 Sept – 1 Oct

$6,162 AUD total

Home in Seabrook

5.0 out of 5 average rating, 3 reviews

Seabrook Beach /136B Fnkln St-June & Aug 31-Sept 7

8 – 15 June

$3,712 AUD total

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Apartment rentals with breakfast

Guest favourite

Apartment in Salem

4.96 out of 5 average rating, 157 reviews

The Creaky Cauldron-Wizards and Witches Welcome!

10 – 17 Jan

$3,271 AUD total

Guest favourite

Apartment in Boston

4.94 out of 5 average rating, 336 reviews

Sunny Private Studio Aptmt

10 – 15 Aug

$1,494 AUD total

Guest favourite

Apartment in Boston

4.97 out of 5 average rating, 217 reviews

Welcoming 2 Bedroom Apt - Close proximity to MBTA

12 – 19 Nov

$2,272 AUD total

Guest favourite

Apartment in Boston

4.92 out of 5 average rating, 267 reviews

Apartment 1BR mins from JFK/UMASS on Red Line

26 Oct – 2 Nov

$2,448 AUD total

Guest favourite

Apartment in Revere

4.96 out of 5 average rating, 153 reviews

Quiet Neighborhood Luxury Stay

10 – 17 Feb

$3,030 AUD total

Guest favourite

Apartment in Salem

4.96 out of 5 average rating, 24 reviews

The Ghoul’s Attic @ The Creaky Cauldron—New Reno!

31 Jan – 7 Feb

$2,371 AUD total

Guest favourite

Apartment in Newbury

4.95 out of 5 average rating, 58 reviews

Moonshadow. A Quaint Beachside Loft near Beach

26 Sept – 3 Oct

$4,321 AUD total

Guest favourite

Apartment in Boston

4.95 out of 5 average rating, 79 reviews

Garden Apt - Highland Park/Fort Hill (Orange Line)

14 – 21 July

$2,333 AUD total

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Bed and breakfast rentals with breakfast

Guest favourite

Apartment in Dedham

4.95 out of 5 average rating, 154 reviews

Two bedrooms, full bathroom, and breakfast room

17 – 24 Sept

$2,479 AUD total

Guest favourite

Room in Rockport

4.93 out of 5 average rating, 320 reviews

Seaside Gardens guest room private floor by beach

25 Oct – 1 Nov

$1,905 AUD total

Guest favourite

Room in Boston

4.95 out of 5 average rating, 292 reviews

Fenway Park Brownstone B&B-3B (Single guest only)

21 – 28 Jan

$1,564 AUD total

Guest favourite

Place to stay in Quincy

4.88 out of 5 average rating, 110 reviews

2 cozy twin bed，free breakfast，5 min to T

30 Sept – 7 Oct

$1,107 AUD total

Guest favourite

Room in Arlington

4.98 out of 5 average rating, 253 reviews

Arlington Craftsman Blue Room, Int. Well Restored

25 June – 2 July

$1,186 AUD total

Superhost

Room in Cambridge

4.84 out of 5 average rating, 153 reviews

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

16 – 23 Oct

$1,408 AUD total

Guest favourite

Room in Cambridge

4.99 out of 5 average rating, 264 reviews

Smack dab between Harvard+Porter 2

13 – 20 Oct

$1,519 AUD total

Superhost

Room in Sudbury

4.79 out of 5 average rating, 279 reviews

Private Cabin in the Woods near river

14 – 21 Aug

$1,366 AUD total

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Quick stats about holiday rentals with breakfast included in Gloucester

Total rentals
20 properties
Local attractions
Beauport Hotel Gloucester, Cape Ann Whale Watch and 7 Seas Whale Watch
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
20 properties include access to Wi-Fi
Total number of reviews
2.3K reviews
Nightly prices starting at
$107 AUD before taxes and fees

Holiday rentals with breakfast in Gloucester

Top-rated Holiday Accommodation with Breakfast in Gloucester

Holiday rentals for every style

Cottages

Houses

Apartments

Popular amenities for Gloucester Holiday Accommodation with Breakfast

Holiday House Rentals with breakfast

Home in Ipswich

Home in Maynard

Home in Winthrop

Home in Hampton

Home in Kittery

Home in Gloucester

Home in Newburyport

Home in Seabrook

Apartment rentals with breakfast

Apartment in Salem

Apartment in Boston

Apartment in Boston

Apartment in Boston

Apartment in Revere

Apartment in Salem

Apartment in Newbury

Apartment in Boston

Bed and breakfast rentals with breakfast

Apartment in Dedham

Room in Rockport

Room in Boston

Place to stay in Quincy

Room in Arlington

Room in Cambridge

Room in Cambridge

Room in Sudbury

Quick stats about holiday rentals with breakfast included in Gloucester

Total rentals

Local attractions

Popular amenities

Wi-Fi availability

Total number of reviews

Nightly prices starting at

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