Rockport, MA Vacation Rentals

Our Favorite Vacation Rentals in Rockport

  • Vintage Rockport Escape
     Country House
    Booking.com
    From
    $172
  • Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet
    ExcellentCottage
    HolidayLettings
    From
    $195
  • Annetti's Watch
     Country House
    Booking.com
    From
    $385
  • Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean
     3br Home/Apartment
    HolidayLettings
    From
    $354
  • Serenity
     Country House
    Booking.com
    From
    $142
  • Waterfront 2 Bedroom !
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $352
  • Manchester by the sea
     Family Stay
    Booking.com
    From
    $100
  • Close to Half Moon Bay
    ExcellentHome/Apartment
    HolidayLettings
    From
    $205

Check prices for these upcoming dates

Rockport Vacation Rentals with Wi-Fi

  • The Smith House in Rockport - a seaside village
    ExcellentCountry House
    Airbnb
    From
    $107
  • The Smith House in Rockport, a seaside village
    ExcellentCountry House
    Airbnb
    From
    $96
  • The Captain's Cottage
    Excellent2br Home/Apartment
    Airbnb
    From
    $170
  • MayBelle's Good Harbor Beach House
    Excellent3br Home/Apartment
    Airbnb
    From
    $424

Rockport Pet-Friendly Vacation Rentals

  • One Bedroom Loft Apartment B at Cedar Hill Farm B & B
    ExcellentHome/Apartment
    HolidayLettings
    From
    $220
  • Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown
     3br Home/Apartment
    HolidayLettings
    From
    $311
  • Stunning classic family home that has central AC & Outdoor patio W/ kitchen & TV
     4br Home/Apartment
    HolidayLettings
    From
    $332
  • Wingaersheek Beach House (Private)
    Excellent6br Home/Apartment
    Airbnb
    From
    $2,189

Rockport Travel Guide

Rockport is a historic coastal town in Massachusetts that offers an outdoor getaway you won’t forget. There are miles of beaches for a leisurely stroll and woods you can go hiking through, as well as boasting a picturesque harbor. There are also lots of art galleries in Rockport due to the city’s seaside beauty and, as you can imagine, seafood is the main local cuisine here. Of course, there are plenty of casual and fine-dining options offering ocean views. Downtown Rockport is ideal for shopaholics to discover unique handcrafted jewelry, crafts, gifts, and clothing stores.

Things to Do in Rockport

Tourists love a trip to Bearskin Neck in Rockport where there's everything from art galleries and shops to views of Rockport Harbor. All of these places are in old fishermen shacks that have been converted. There are fantastic views out to the Atlantic Ocean at The Point, while at Pebble Beach you can walk along the sand and admire the sea. Alternatively, head to Front Beach, near to shops and restaurants. A famous spot for tourists is the Motif Number 1, a red fishing shack that is the most painted building in the world and something you could only find at the seaside. It's a great photo opportunity and can be spotted around Rockport. You can even get a boat out to Thatcher’s Island, where there are two twin lighthouses. Instagrammers be ready!

Best Places to Stay in Rockport

Rockport is known for its welcoming hospitality and visitors can find everything from cozy inns to budget motels.

Best Time to Visit Rockport

For sunshine and hot temperatures, the months of June, July, and August are a winner in Rockport. There is also pleasant weather during spring for this lovable costal spot.

Price and Availability in Rockport

Most expensive
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The cheapest day to stay at a vacation rental in Rockport tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Rockport tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Rockport is in August, while the cheapest month is in December. The most popular time to book a vacation rental in Rockport is in the high season in August. Rockport has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Rockport

Rainy days
64°
3
69°
3
76° 22°
6
86° 34°
3
84° 45°
5
95° 53°
4
92° 47°
3
89° 37°
1
78° 33°
6
71° 16°
4
61°
7
59°
3
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Rainy days

This climate histogram shows you the weather patterns in Rockport. The warmest months in Rockport are June and May, when temperatures reach 95 ˚F. The coolest month is December, when temperatures drop to 2 ˚F. The wettest month in Rockport is January with 6.6 inches of rain, while the driest month is April with 1.32 inches of rain.

What Expert Travelers Think

  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker

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