50 Best Rockport Apartments on Holiday Lettings - Vacation rentals

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195 Vacation rentals

(5) Excellent 

12

Vacation b&b in Rockport

Cape Ann / Rockport

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
BOOKING ACCEPTED NOW FOR SUMMER 2018!!. DEDICATED OFF-STREET PARKING FOR ONE CAR. BEST LOCATION IN ROCKPORT steps away from everything! Ground floor studio boasts comfortable and clean efficiency with AC, cable TV and microwave kitchenette, private entrance, private b …see more

from $125 / night

$950 / week

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Responds fast!
avg. 1 hour 56 minutes

from $125 / night

(5) Excellent 

17

Vacation home in Rockport

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Sitting directly on picturesque Long Beach, this is the perfect spot for a romantic get-away or a family retreat. With decks in the front and back of the house, sun-chasers and shade-seekers alike will be pleased at any time of day. The cottage is sunny and open with a …see more

from $350 / night

$2,200 - $2,800 / week

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from $350 / night

(1) Excellent 

14

Vacation cottage accommodation

Cape Ann / Rockport

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Walk to the water from this cozy peaceful cottage with ocean views. This bright and cheerful recently updated vintage cottage is just minutes from nearby beaches. Enjoy beautiful sunrises, birds chirping, and leisurely strolls along the rugged coast. Stunning views of t …see more

from $180 / night

$1,280 - $1,400 / week

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from $180 / night

(2) Very Good 

12

Vacation home in Rockport

Cape Ann / Rockport

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Private garden
Beachcomber Room, at Changing Tides Bed and Breakfast, features a comfortable king sized bed or 2 twin beds, and an ensuite bathroom. This sunny room has 2 sky lights, a ceiling fan, AC, a sitting room with a small refrigerator, and a shared bathroom. Stay includes da …see more

from $175 / night

$892 / week

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Responds fast!
avg. 2 hours 48 minutes

from $175 / night

18

Vacation apartment with golf nearby in Rockport

Cape Ann / Rockport

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
The Seaward offers a spectacular setting and charming accommodations. Loblolly Cove, offers accommodations for up to 4 people. One bedroom has a queen sized bed, while the rather spacious living room has accommodations for two more. At Loblolly Cove, you will enjoy a …see more

from $183 / night

$1,275 - $1,345 / week

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Responds fast!
avg. 45 minutes

from $183 / night

(30) Excellent 

Certificate of Excellence

23

Vacation cottage with golf nearby in Rockport

Cape Ann / Rockport

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Car not necessary
OPEN YEAR ROUND - 2 night minimum stay. 2018... we're honored to celebrate our 9th year hosting guests from all over the world! PERIWINKLE COTTAGE - truly a place to call "a home away from home". This 2-unit, townhouse cottage offers guests privacy and an updated sea …see more

Certificate of Excellence

from $125 / night

$875 / week

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from $125 / night

25

Vacation home in Rockport

Cape Ann / Rockport

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Ask about children
Enjoy the comforts of modern day living while you step back in time in this updated colonial-era vacation rental home. From the moment you turn the brass door knob, which is original to the house, you will feel steeped in history. Filled with light from the large wind …see more

from $360 / night

$1,780 - $2,230 / week

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from $360 / night

11

Vacation home in Rockport

Cape Ann / Rockport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Quaint cozy pre-Revolutionary house with priceless view of picturesque Rockport village and Atlantic Ocean. Located on quiet dead-end lane next to tranquil pond and small town park. Two-minute walk to beach and town's attractive Main street with shops, art galleries and …see more

from $143 / night

$1,200 / week

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from $143 / night

(3) Excellent 

14

Rockport Vacation b&b rental

Cape Ann / Rockport

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Air conditioning
Captain's Quarters,at Changing Tides Bed and Breakfast, features a queen-sized bed, two skylights and a shared bath, sleep well and look forward to a gourmet breakfast. Beaches, downtown shops and galleries are all within a short walk of our home. This room is located …see more

from $160 / night

$1,120 / week

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Responds fast!
avg. 2 hours 48 minutes

from $160 / night

(2) Excellent 

18

Vacation cottage in Rockport

Cape Ann / Rockport

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Seamist Cottage is located on a private yard in historic downtown Rockport, Massachusetts, a charming seaside community. Short walks to shopping and art galleries on Bearskin Neck, beaches, train station as well as the Shalin Liu Perfomance Center. We, as new owners, w …see more

from $115 / night

$725 - $1,295 / week

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Responds fast!
avg. 2 hours 26 minutes

from $115 / night

23

Vacation home rental

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
Midway between two picturesque places, the seaside village of Rockport and the historic fishing port of Gloucester, Sage Hill is the perfect vacation destination. Walk to Long Beach (it’s about a 5 minute walk), or take a short drive to Good Harbor Beach. Sage Hill …see more

from $442 / night

$2,030 - $2,780 / week

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from $442 / night

36

Vacation home in Rockport

Cape Ann / Rockport

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Pet friendly
This waterfront vacation rental is a wonderful inviting family vacation home with bountiful space, located in the highly desirable area of "The Avenues" at the northern end of Rockport. Boasting 5 bedrooms/3.5 baths and the ability to comfortably sleep 12 people, this i …see more

from $790 / night

$3,930 - $5,530 / week

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from $790 / night

20

Vacation cottage in Rockport

Cape Ann / Rockport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Pet friendly
This delightful summer vacation rental cottage, overlooking broad stretches of the Atlantic Ocean and Rockport's Hoop Pole Cove, is a perfect retreat for anyone looking to experience the best of New England. The wraparound porch and expansive yard allow you to fully enj …see more

from $290 / night

$1,430 - $2,030 / week

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from $290 / night

31

Vacation home in Rockport

Cape Ann / Rockport

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly
This inviting family vacation home has bountiful space and is located in the highly desirable area of "The Avenues" at the northern end of Rockport. Boasting 6 bedrooms, 3.5 baths and the ability to comfortably sleep 10 people, this is a house for the extended family to …see more

from $559 / night

$2,630 - $3,405 / week

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from $559 / night

(3) Excellent 

15

Vacation b&b in Rockport

Cape Ann / Rockport

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 0.1 mi
  • Car not necessary
  • Air conditioning
Are you looking for a conveniently located affordable place to stay while you enjoy all that Rockport has to offer? Are you traveling with family or friends and would like the privacy of separate rooms? Our top floor guest rooms (2 available) are perfect for travelers …see more

from $95 / night

$665 / week

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Responds fast!
avg. 1 hour 56 minutes

from $95 / night

19

Vacation apartment in Rockport

Cape Ann / Rockport

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
  • Pet friendly
All that Rockport has to offer is within a short walk from this completely remodeled property located in the picturesque Historic District. This vacation rental home gleams with modern amenities yet retains the charm of the original house, which dates from the 1800’s. O …see more

from $297 / night

$1,530 - $1,830 / week

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from $297 / night

15

Rockport Vacation apartment rental

Cape Ann / Rockport

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
The Building was once the historic Sail loft- oozing with character and charm. Inside is a 2 Bedroom, 1 Bath apartment unit. A good sized living area with a leather couch, TV & dining table that can fit up to 6. There is a small patio in front with a table, bench and 2 …see more

from $155 / night

$975 - $1,185 / week

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Responds fast!
avg. 1 hour 56 minutes

from $155 / night

(2) Excellent 

18

Vacation cottage rental

Cape Ann / Rockport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Formerly Seaward Inn, "The Seaward" continues to offer a spectacular setting and charming accommodations. Here you can fully relax while listening to the ocean waves. Experience the charm, serenity, and unspoiled beauty that is The Seaward. Suite 205, also known as Gu …see more

from $169 / night

$1,495 - $1,635 / week

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Responds fast!
avg. 45 minutes

from $169 / night

(5) Excellent 

21

Vacation apartment in Rockport

Cape Ann / Rockport

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
The Salty Dog Summer Stay is a spacious, bright, furnished apartment with all the comfort and amenities one may need to enjoy time in our seaside town. Perfectly located on Atlantic Avenue in the Old Garden Beach neighborhood, many of Rockport's shops, restaurants, and …see more

from $153 / night

$209 - $2,494 / week

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from $153 / night

35

Home rental in Rockport

Cape Ann / Rockport

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This unique beachfront vacation home has been completely remodeled but retains hints of its historical importance; it was the original U.S. base for the first Trans-Atlantic Cable in 1884. Originating in Ireland, the cable went from Nova Scotia to Cape Ann and back to F …see more

from $888 / night

$3,780 - $5,681 / week

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from $888 / night

(2) Excellent 

15

Vacation home in Rockport

Cape Ann / Rockport

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets
Cozy, bright , and ideally located. Unrestricted view of ocean from back of house and large deck. Walk across to Back Beach, 5 minute walk to Front Beach and Main Street downtown. Large fenced yard across from ocean. Beautiful sunrises and sunsets. Train Station 1/2 mil …see more

from $429 / night

$3,000 / week

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from $429 / night

26

Home accommodation in Rockport

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This charming vacation rental home is situated just 300 yards from Whale Cove. Walk just 1 mile to a sandy beach or into the village of Rockport with its shops, restaurants, galleries and a world class Performance Center. Choose to cook your lobsters in the large, upd …see more

from $401 / night

$1,830 - $2,480 / week

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from $401 / night

28

Vacation cottage in Rockport

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This sweet and comfortable vacation rental cottage is just across the street from Folly Cove, one of the most striking coves on Cape Ann. The living room has views of the water (just across the street) and off of the living room is a nice screened porch with views an …see more

from $310 / night

$1,530 - $2,130 / week

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from $310 / night

23

Vacation home in Rockport

Cape Ann / Rockport

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Ask about children
Granite Pier is a traditional Cape Ann home with an unusual history. Built in the mid to late 1800’s, it was part of the Rockport Granite Company housing workmen who mined the nearby quarries. Blending traditional craftsmanship with modern amenities, this home is quinte …see more

from $550 / night

$2,730 - $3,241 / week

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from $550 / night

(1) Very Good 

15

Vacation home rental

Cape Ann / Rockport

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Private garden
$1750 (off season) - $2,100 (peak season) per week .... Fresh sea breezes keep the inside cool during the summer and a large fireplace in the living room makes this a cozy winter getaway. The home comfortably sleeps five, has a completely furnished kitchen, a dining roo …see more

from $250 / night

$1,750 - $2,100 / week

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Responds fast!
avg. 3 hours 23 minutes

from $250 / night

24

Vacation home rental

Cape Ann / Rockport

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Rockport Village House is a charming vacation rental home that offers versatility, style and convenience. Located on a quiet, residential street and a short walk to all that Rockport has to offer: beautiful ocean vistas, beaches, galleries, restaurants, shops and train …see more

from $410 / night

$2,030 - $2,830 / week

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from $410 / night

(1) Excellent 

16

Home rental in Rockport

Cape Ann / Rockport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
This delightful vacation rental cottage is located on a quiet Rockport lane less than 100 yards from the sands of Cape Hedge Beach. Just cross the lane and walk over the footbridge and you're on the beach! This cozy two bedroom beach house is pine-paneled, in the tra …see more

from $285 / night

$1,405 - $1,845 / week

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from $285 / night

22

Vacation home in Rockport

Cape Ann / Rockport

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Ask about children
This spacious 5 BR vacation rental home is steps from Old Garden Beach as well as a short stroll into the seaside village of Rockport. Make this delightful house your home base for your beach escape this summer. The main level of the home consists of the gracious and …see more

from $810 / night

$4,030 - $5,030 / week

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from $810 / night

21

Rockport Vacation home rental

Cape Ann / Rockport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This spacious and fully air conditioned vacation home boasts a lovely landscaped in-ground pool in a private, fenced-in yard. In the center of charming Rockport, the home is only two blocks from Old Garden Beach and Rockport harbor. A short stroll takes you to Bearskin …see more

from $738 / night

$3,230 - $4,530 / week

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from $738 / night

16

Cottage rental in Rockport

Cape Ann / Rockport

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Pet friendly
From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or walk down the quiet lane to Granite Pier and experience the unsurpassed views of the sun rising over the Atlantic Ocean, and of fishing boats moored nearby. The full moon over Granite Pier …see more

from $230 / night

$1,130 - $1,480 / week

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from $230 / night

15

Vacation condo in Rockport

Cape Ann / Rockport

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Air conditioning
You can't get any closer to New England charm than this condo, called Four Winds, located on Tuna Wharf off Bearskin Neck in Rockport, MA. The view looks directly over the water and is truly picturesque. This is a great place for a getaway providing the choice of cook …see more

from $250 / night

$1,750 / week

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Responds fast!
avg. 2 hours 25 minutes

from $250 / night

(1) Excellent 

24

Vacation cottage in Rockport

Cape Ann / Rockport

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Ask about pets
Down a quaint lane you will find an Artists cottage and guest suite. The smaller of the two buildings contains a private double bed retreat with en suite, cable TV & Wi fi. The Main house boasts a charming loft bedroom with 2 ex-long twin beds. The ceiling of the second …see more

from $186 / night

$1,300 / week

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from $186 / night

(1)  

41

Vacation home in Rockport

Cape Ann / Rockport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
From its waterfront perch, this 4BR vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectacular, unobstructed views of Sandy Bay. The location of the home is ideal, away from all the hustle of town, but within a 10-15 minute walk to ever …see more

from $660 / night

$3,280 - $4,705 / week

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from $660 / night

33

Vacation home in Rockport

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
Rockport oceanfront! This sunlit vacation rental home couldn’t be closer to the water, situated on a bluff overlooking Sandy Bay and Pigeon Cove Harbor. Popples Cove House offers everything you could hope for in a vacation getaway – scenic views, location, privacy, comf …see more

from $672 / night

$3,230 - $4,551 / week

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from $672 / night

21

Vacation home in Rockport

Cape Ann / Rockport

3 9 3 nights min

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min
  • Ask about children
  • Pet friendly
If you are looking for a beach house, this is it. Walk to Long or Cape Hedge beaches in 5 minutes or just relax at this fun vacation rental home and enjoy the water views from one of two decks. Sea Vagabond House is actually two houses in one; the original cottage downs …see more

from $245 / night

$1,205 - $1,539 / week

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from $245 / night

(4) Excellent 

20

Vacation home in Rockport

Cape Ann / Rockport

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Located across from Rockport's Front Beach, Beach & King Beach House is an intimate Cape Ann home located on the North Shore in Massachusetts. Accommodations at our Rockport home offer a picturesque setting with stunning ocean views and a 5-minute stroll to historic Bea …see more

from $615 / night

$4,300 - $7,800 / week

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from $615 / night

(1) Excellent 

28

Rockport Vacation home rental

Cape Ann / Rockport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
Enjoy the best of all worlds in this spacious and bright vacation rental home overlooking Rockport's stunningly picturesque Flat Ledge Quarry. Not only can you walk to town or to the beach in a few minutes, but the property includes full deeded swimming rights to Little …see more

from $450 / night

$2,230 - $2,930 / week

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from $450 / night

23

Vacation home in Rockport

Cape Ann / Rockport

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
2017 Season-June through September- Aug 26 to Sept 9 (2 weeks in a row); Directly on the Atlantic with spectacular ocean views opposite Thatcher’s Island’s Twin Lights. Relax on the wooden deck off the 16 foot sliding glass doors from the living room/dining room. On …see more

from $358 / night

$2,500 / week

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from $358 / night

24

Vacation home in Rockport

Cape Ann / Rockport

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Labor Day Week- First week in September still AVAILABLE. from 9/2 to 9/9 - Book now ! Unobstructed OCEAN VIEW from every window! 3 BR HOUSE WEEKLY VACATION RENTALS - The Glenellen Cottage Delightful, late 1800's, newly renovated kitchen with 1st & 2nd floor full …see more

from $358 / night

$2,500 / week

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from $358 / night

(1) Excellent 

17

Vacation home in Rockport

Cape Ann / Rockport

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning
Back Beach Cottages are a unique 2 cottage property with stunning views of the ocean. The location offers the best of both worlds: it's a quiet and relaxing spot for enjoying the beach and also close to downtown Rockport. The homes are steps away from Back Beach, a 5 mi …see more

from $456 / night

$3,186 / week

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from $456 / night