Holiday rentals with a patio in Gloucester

Find and book unique rentals with patio on Airbnb

Top-rated rentals with patio in Gloucester

Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Rockport

5.0 out of 5 average rating, 29 reviews

Little Apartment by the Sea

Small completely furnished apt. for 1 or 2. Beautiful scenic Rockport, MA. Seconds from Back Beach & min. from Front Beach. 10 min. walk to Train to Boston. Small kitchen. Living/ bedroom combo. 2 twin beds. 43" flat screen. Dishwasher. A/C. Washer/dryer. Parking for 1 car. Patio table & chairs for picnicking. 5 minutes to Bearskin Neck for shopping, restaurants & art galleries. No pets. No smoking. No handicapped access. Stairway with railings to walk down to the yard & apt. 3 night minimum.

4–11 Oct

$195 SGD per night

Guest favourite

Guest suite in Burlington

4.98 out of 5 average rating, 204 reviews

Relaxing 2 Room Suite with Private Bath/Deck/Patio

Welcome to this spacious, quiet and relaxing furnished suite (private entrance own deck- patio-fire pit). It is truly in an amazing location; walking distance to Mall/Lahey Hospital & only 18 mi from Boston Logan Airport, with plenty of parking. Our place is good for professionals, students, couples, solo, families (with kids). The airbnb is attached to a main house but it's contactless (check-in/-out) with own entrance. Ideal for 2, a little tight for 3 but manageable (sofa into bed).

28 Feb – 7 Mar

$134 SGD per night

Guest favourite

Flat in Gloucester

5.0 out of 5 average rating, 20 reviews

Cozy Apartment at Green Landing in Gloucester

Take it easy at this unique, tranquil and cozy getaway in Gloucester. Enjoy two floors of living space overlooking the changing tides and natural wildlife of the Green Landing Salt Marsh. This stylish and cozy one bedroom apartment is centrally located within a short drive to both of Gloucester’s iconic beaches. A 1-2 minute drive to route 128, and walking distance to the Train Station means guests can easily access all of Gloucester, as well Rockport, Salem and Boston, with or without a car.

30 Aug – 6 Sep

$245 SGD per night

Superhost

Flat in Gloucester

4.81 out of 5 average rating, 54 reviews

Lovely 2br Cherry apt in Gloucester / Free parking

Have fun with the whole family at this cute place and enjoy what Gloucester have to offer !! Here at our place you will be centrally located off Route 128 just minutes away from many wedding venues and golf clubs Good Harbor, Niles, Pavilion, Half Moon and Wingaersheek beaches, year round nature walks, downtown shops and restaurants, grocery stores, and the commuter rail to Boston. Enjoy a great base for exploring Cape Ann with drives to Salem, Essex, or Manchester by the Sea, to name a few!

7–14 May

$209 SGD per night

Guest favourite

Guest house in Beverly

4.98 out of 5 average rating, 112 reviews

Adorable 1-bedroom carriage house

Kick back and relax in this quaint refurbished carriage house, centrally located in Beverly, Massachusetts. The first floor offers a kitchen space (complete with a toaster oven and mini fridge) and a dining area, as well as a spacious living room set that is perfect for nights in after a day of exploring. If you prefer, the patio also has cozy outdoor seating! Upstairs, you can find a comfortable Queen-sized bed, a private bathroom, and a desk space that's perfect for working from home.

23–30 Nov

$251 SGD per night

Guest favourite

Guest suite in Gloucester

5.0 out of 5 average rating, 44 reviews

Sunsets at the Seawall - A Coastal Hideaway

Beautiful, serene studio apartment steps from the water & colorful sunsets of Lane’s Cove in Gloucester. Includes kitchen, bathroom & comfortable bedroom with separate sitting area. A private patio just outside has a tabletop grill & an outdoor dining area. A short walk to Lane’s Cove, Plum Cove Beach, or the North Woods. A 10-20 min drive will take you to downtown Rockport , or Gloucester, for great seafood, art, and shopping! Enjoy a restful retreat or find adventure on Cape Ann!

6–13 Jan

$262 SGD per night

Guest favourite

Flat in Beverly

4.93 out of 5 average rating, 136 reviews

Entire 1st floor apt in charming seaside Beverly

Enjoy a stylish experience at this centrally-located place. Easy access to downtown Beverly, Salem, local beaches, and commuter rail to Boston. Apartment features a fully furnished living room, bedroom, and kitchen, along with extra amenities including a/c, 𝖶𝗂𝖥𝗂, cable, front and back porch, and outdoor fireplace and patio. Walking distance to all that downtown Beverly has to offer One train stop or 5 minute drive to downtown Salem

3–10 Apr

$187 SGD per night

Guest favourite

Apartment in Gloucester

4.95 out of 5 average rating, 61 reviews

Luxurious beach house w/ harbor views & near beach

There isn't a better location on Cape Ann! Rocky Neck is the oldest art colony in the US. This luxurious 1br boasts ocean views & was updated w/ designer & custom features. Not only can you walk to the beach, there are amazing restaurants across the street and a wine & cheese bar featuring local art you can peruse while having a cocktail. Come and enjoy sunsets from the deck and everything else Gloucester has to offer!

28 Aug – 4 Sep

$331 SGD per night

Superhost

Flat in Ipswich

4.82 out of 5 average rating, 117 reviews

2b apt loft downtown Ipswich

When you get in to this apt/loft you will be amazed by the comfort and cozy set up. This unit is located downtown Ipswich on the third floor with a beautiful view where you can enjoy sunsets and have a place to hang out. NOT RECOMMENDED for elderly people because of the stairs. there are three sets of stairs, also if you are traveling with young children or toddlers need to be aware of the height and the whereabouts.

16–23 Feb

$224 SGD per night

Guest favourite

Loft in Gloucester

4.98 out of 5 average rating, 103 reviews

Downtown, Shops, Beach, Deck, Coffee Bar

Escape to the charming heart of Gloucester with this quaint and comfortable one-bedroom retreat, perfect for couples seeking for a rejuvenating getaway. Nestled in the heart of downtown, this enchanting home boasts a prime location just moments from the city's finest restaurants, shops, and attractions.

28 Jan – 4 Feb

$329 SGD per night

Guest favourite

Loft in Derry

4.97 out of 5 average rating, 99 reviews

The Carriage House, A Retro Loft

Welcome to our newly renovated and restored historic Carriage House for your next stay in Southern New Hampshire! Book your New England stay now at The Carriage House to enjoy the beautiful NE coasts, gorgeous fall foliage, all within 40 minutes of Boston.

22–29 Oct

$165 SGD per night

Guest favourite

Guest suite in Gloucester

5.0 out of 5 average rating, 91 reviews

Walk to Good Harbor Beach and Downtown Gloucester

Enjoy this separate entrance fully private apartment within easy walking access to Good Harbor beach, downtown Gloucester, and everything Cape Ann and the North Shore has to offer! This quiet and cozy place has everything you need for your sea-side stay.

22–29 Sep

$256 SGD per night