Holiday rentals in Rockport

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Top-rated holiday rentals in Rockport

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Guest favourite

Apartment in Rockport

4.99 out of 5 average rating, 185 reviews

6 Tuna Wharf - Harbor right outside kitchen door!

Dreaming of summer vacation in Rockport? This condo is in the middle of the action and excitement of Bearskin Neck yet private & directly on the wharf. Classy beachy condo overlooking Rockport Harbor & Motif 1. Steps from shops, beaches, restaurants, art galleries & beaches. Outside the kitchenette, a private patio on the wharf for morning coffee, grilling or evening happy hour. Relax and watch the boats go by year round! A fun getaway even in the off season. Book early to secure your trip!

26 Aug – 2 Sep

$494 SGD per night

Guest favourite

Loft in Rockport

5.0 out of 5 average rating, 197 reviews

Chic Downtown Loft ☆ Private Parking ☆ Ocean View

Enjoy the coastal and seaside views from the renovated and bright "jewel" located in the charming seaside New England town of Rockport on Cape Ann. The loft is centrally located is literally steps to the beaches, the Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu. 1-min walk to Bearskin Neck & Motif No.1 5-min walk to Front Beach + easy access to many others 8-min drive to Halibut Point Park 25-min drive to Salem 1-hour drive to Boston 15-min walk MBTA Train Station

27 Nov – 4 Dec

$243 SGD per night

Guest favourite

Guest suite in Gloucester

4.94 out of 5 average rating, 35 reviews

Live Like a Local, Just Steps From The Beach

Beautiful and private 2 bedroom suite, located on the upper floor of stylish 19th century beach house. Steps (literally steps) from Plum Cove Beach and Lanes Cove you'll have choices of where to swim or watch the sunset over the water. Guests will have the entire 2nd floor, with a private entrance and is western facing for beautiful sunset views. Located within a 15 minute drive to downtown Rockport, Gloucester, Wingaersheek and Good Harbor Beaches. 30 minutes from Salem for Halloween fun!

5–12 Feb

$127 SGD per night

Guest favourite

Apartment in Rockport

4.99 out of 5 average rating, 143 reviews

Bearskin Neck Rockport ★ Amazing Views ★ Parking

From the deck of this New England vacation retreat enjoy amazing views of Rockport Harbor and the iconic Motif #1. Steps from delightful shops, restaurants, and ice cream & coffee shops, this recently updated 1-bedroom, 1-bathroom condo with rare, on-site parking is located in the heart of Rockport right on Bearskin Neck. Enjoy beautiful ocean breezes sipping coffee or cocktails on the deck of this sweet beach retreat nestled on the Atlantic coast. Come fall in love with charming Rockport!

11–18 Dec

$403 SGD per night

Guest favourite

Loft in Gloucester

4.9 out of 5 average rating, 167 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2024! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

22–29 Dec

$167 SGD per night

Guest favourite

Flat in Rockport

4.94 out of 5 average rating, 148 reviews

Mary's By The Sea

A unique 650 square foot ground floor apartment across the street from Front Beach. A 6 minute walk from the Rockport Commuter Train Station, MBTA. We have an in town location . There is a separate bedroom with a queen mattress and a pullout sofa bed in the living area. The pullout sofa is most ideal for teens or smaller kids .There is a bathroom with a sink and toilet. There is another room with a sink and shower. We provide one parking spot next door at The Cove parking lot.

29 Mar – 5 Apr

$261 SGD per night

Guest favourite

Tiny home in Rockport

4.94 out of 5 average rating, 128 reviews

Little Red House on Bearskin Neck!

Rockport is a lovely seaside town just 40 miles northeast of Boston at the tip of Cape Ann. It is a small peninsula surrounded by the Atlantic Ocean known for its beaches, seafood, art, and one of a kind shopping. Full of beauty&serenity RCKPT invites you to slow down. Of course you can come explore too! There is no shortage of beaching, swimming, sailing, trailing, kayaking, paddle boarding and diving . The Lil House sits in the center of it all (the neck!) Beauty awaits!

2–9 Jun

$282 SGD per night

Guest favourite

Home in Rockport

4.97 out of 5 average rating, 281 reviews

Charming Toe-Hold, A Short Walk to Town and Beach

Toe-Hold is a wonderful year-round 1846 home with plenty of rooms, reading nooks and quiet spaces for family and friends of all backgrounds to eat and play together. The gorgeous beaches and picturesque downtown, great restaurants, art galleries and shops for the whole family, are within 10-15 minute walk. Rockport is one of the oldest art colonies in the US, and home to generations of fishermen. Day trips by car or train to Boston and other beautiful historic towns.

7–14 May

$388 SGD per night

Guest favourite

Flat in Rockport

4.96 out of 5 average rating, 256 reviews

1 Bedroom Apartment By Harbor - Centrally Located

Newly renovated, beautiful 1 bedroom second level apartment located right in the heart of Rockport with an unbeatable location next to the harbor. There is a deck you can relax on with a view of the harbor. Right in downtown Rockport, you are only steps away from Bearskin Neck and the shops, restaurants and stunning beaches. Please note - you will need to climb stairs to access the apartment, and as it is downtown it can be bustling and get noisy.

23–30 Jul

$283 SGD per night

Guest favourite

Guest suite in Rockport

4.99 out of 5 average rating, 608 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.

19–26 Mar

$171 SGD per night

Guest favourite

Flat in Rockport

4.9 out of 5 average rating, 144 reviews

Sweet short term rental in Rockport

Lovely hilltop unit located on private wooded property, steps away from 2 beaches. Built on a massive granite boulder, the property is one of kind with stunning seasonal views of the Atlantic. Fully equipped kitchen, flat screen TV, WiFi, and everything to make your stay pleasant and comfortable. We're a 7 minute drive from downtown Rockport and Gloucester, a 7 minute walk to Cape Hedge and Long Beaches.

17–24 Apr

$208 SGD per night

Guest favourite

Apartment in Rockport

4.89 out of 5 average rating, 37 reviews

In Town One Room Studio-Walk to Shops/Beaches

Furnished one room studio apartment. No separate sleeping area, futon doubles as a queen bed. Compact but everything you need for your stay! Parking for one car is a short walk from the unit. Walking distance to town center and beaches. Perfect for 1-2 people looking for a quiet stay in this beautiful seaside town. Come and enjoy all there is to offer in this beautiful and inspiring community.

2–9 Oct

$156 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Rockport holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Rockport's top sights

Roy Moore Lobster Co45 locals recommend

Roy Moore's Fish Shack Restaurant26 locals recommend

The Lobster Pool44 locals recommend

Rockport Music-Shalin Liu Performance Center77 locals recommend

Long Beach Gloucester10 locals recommend

Pebble Beach6 locals recommend

Other great holiday rentals in Rockport

Guest favourite

Flat in Rockport

5.0 out of 5 average rating, 29 reviews

Little Apartment by the Sea

9–16 Jul

$191 SGD per night

Superhost

Flat in Rockport

5.0 out of 5 average rating, 3 reviews

NEW Rare Waterfront Luxury Penthouse|Bearskin Neck

13–20 Sep

$491 SGD per night

Guest favourite

Apartment in Rockport

5.0 out of 5 average rating, 30 reviews

Panoramic Ocean Views in Rockport

7–14 Jun

$342 SGD per night

Guest favourite

Guest suite in Rockport

4.99 out of 5 average rating, 92 reviews

King size studio Cape Ann retreat

9–16 May

$221 SGD per night

Guest favourite

Guest suite in Rockport

4.99 out of 5 average rating, 96 reviews

Large Suite in the Historic District of Rockport.

28 Apr – 5 May

$229 SGD per night

Guest favourite

Flat in Rockport

4.95 out of 5 average rating, 39 reviews

Downtown w parking, beach, shops

7–14 Jun

$404 SGD per night

Guest favourite

Cottage in Gloucester

4.97 out of 5 average rating, 99 reviews

Sunny & private cottage in Lanesville Village

20–27 Jan

$234 SGD per night

Guest favourite

Guest house in Rockport

5.0 out of 5 average rating, 58 reviews

Historic Carriage House | Downtown | Dog Friendly

15–22 Dec

$467 SGD per night

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Quick stats about holiday rentals in Rockport

Total rentals	260 properties
Rentals with a pool	10 properties have a pool
Pet-friendly rentals	60 properties allow pets
Family-friendly rentals	150 properties are a good fit for families
Total number of reviews	12K reviews
Nightly prices starting at	$82 SGD before taxes and fees

Holiday rentals in Rockport

Top-rated holiday rentals in Rockport

Apartment in Rockport

Loft in Rockport

Guest suite in Gloucester

Apartment in Rockport

Loft in Gloucester

Flat in Rockport

Tiny home in Rockport

Home in Rockport

Flat in Rockport

Guest suite in Rockport

Flat in Rockport

Apartment in Rockport

Holiday rentals for every style

Flats

Cottages

Houses

Popular amenities for Rockport holiday rentals

Stay near Rockport's top sights

Other great holiday rentals in Rockport

Flat in Rockport

Flat in Rockport

Apartment in Rockport

Guest suite in Rockport

Guest suite in Rockport

Flat in Rockport

Cottage in Gloucester

Guest house in Rockport

Quick stats about holiday rentals in Rockport

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore