50 Best Cape Ann Vacation rentals on Holiday Lettings - Apartments

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Cape Ann

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197 Vacation rentals

(1) Excellent 

6

Cape Ann Vacation apartment rental

Cape Ann / Essex

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
We can now offer Apartment B to our options at Cedar Hill Farm B & B. This apartment is identical to Apt. A also located in our lower barn. The bedroom is on second floor with open to living area and cathedral ceiling. 8 Foot sliders open to open pastures, woods and …see more

from $175 / night

$1,100 - $1,450 / week

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from $175 / night

(1) Excellent 

24

Vacation cottage in Gloucester

Cape Ann / Gloucester

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Enjoy a peaceful retreat in coastal New England by staying at 'Blue Heron Cottage' - a lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby bea …see more

from $199 / night

$1,393 / week

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Responds fast!
avg. 13 minutes

from $199 / night

37

Vacation home in Cape Ann

Cape Ann / Gloucester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Explore one of America's oldest towns during your stay in this sleek home, featuring an upstairs deck for direct access to the Atlantic's fresh air. Central air conditioning and Netflix streaming capabilities invite visitors to unwind after a day exploring rocky shores …see more

from $149 / night

$1,043 / week

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Responds fast!
avg. 2 hours 22 minutes

from $149 / night

(5) Excellent 

17

Vacation home in Cape Ann

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 $400 / night

$2,800 / week

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from $400 / 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

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

18

Cape Ann Vacation home rental

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true wa …see more

from $250 / night

$4,950 / week

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Responds fast!
avg. 1 hour 51 minutes

from $250 / night

(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 39 minutes

from $125 / night

15

Cape Ann 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

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

(32) Excellent 

Certificate of Excellence

23

Vacation cottage with golf nearby in Cape Ann

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

18

Cape Ann Vacation home rental

Cape Ann / Essex

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Ask about children
Built in 1750, this charming vacation rental provides lovely views of the Essex Salt Marsh and is centrally located to everything Essex has to offer. Indigo Blue is steps away from downtown Essex, with its numerous restaurants and a wide assortment of antique shops. Ind …see more

from $210 / night

$1,030 - $1,530 / week

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from $210 / night

(2) Excellent 

7

Home rental in Cape Ann with golf nearby

Cape Ann / Gloucester

5 11 1 night min

  • 5 bedrooms
  • Sleeps 11
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Spacious home located two blocks from Atlantic Ocean and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat in July & August. Large modern fully equipped kitchen with double oven, 5 burner Viking cooktop, dishwash …see more

from $500 / night

$3,500 / week

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Responds fast!
avg. 1 hour 4 minutes

from $500 / night

16

Cape Ann Vacation condo rental

Cape Ann / Manchester-by-the-Sea

3 5 4 nights min

  • 3 bedrooms
  • Sleeps 5
  • 4 nights min
  • Child friendly
Completely renovated 2+ bedroom, 1.25 bath. Second floor unit. Spacious designer kitchen w/ stainless steel appliances. Large Living room and wonderful master bedroom suite. Close to town center, commuter rail, and Singing Beach. 4 minute drive to Singing beach, 20 minu …see more

from $250 / night

$1,750 / week

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from $250 / night

(3) Excellent 

14

Cape Ann 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 49 minutes

from $160 / night

30

Home accommodation in Cape Ann

Cape Ann / Essex

6 14 3 nights min

  • 6 bedrooms
  • Sleeps 14
  • 3 nights min
  • Ask about children
  • Air conditioning
Watch spectacular sunsets over the Essex River from the expansive deck of this one-of-a-kind vacation home. Clamshell Landing sits on 22 acres of pristine conservation land and overlooks the green grasses of the Essex salt marsh. Swim or kayak to the beach or out to lun …see more

from $1,310 / night

$6,530 - $8,830 / week

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from $1,310 / night

28

Vacation cottage in Cape Ann

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 - $2,055 / week

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from $310 / night

(10) Excellent 

46

Vacation apartment in Cape Ann

Cape Ann / Gloucester

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Reservations from June 22 to end of September must be for 7 nights minimum with Check-in on Friday afternoon. The view is spectacular! The apartment is inside a commercial marine building so it's right on top of the water, where the ships come in to unload lobsters an …see more

from $110 / night

$924 - $1,512 / week

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Responds fast!
avg. 3 hours 35 minutes

from $110 / night

21

Vacation home rental

Cape Ann / Rockport

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
Spend your days at the beach or relaxing poolside by your very own private pool. Rockport Hideaway is also only a short distance from Rockport's shopping, dining and family activities. Leave the car and stroll to the village, beaches, schools (with tennis courts and pla …see more

from $410 / night

$2,030 - $2,866 / week

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from $410 / night

(5) Excellent 

14

Apartment rental in Cape Ann

Cape Ann / Gloucester

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around …see more

from $275 / night

$1,850 - $1,900 / week

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from $275 / night

11

Cape Ann Vacation studio rental

Cape Ann / Gloucester

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. One block walk to Good Harbor Beach and scenic Back Shore. We call your home awa …see more

from $165 / night

$975 / week

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from $165 / night

(1) Excellent 

28

Cape Ann 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 - $2,905 / week

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from $450 / night

25

Gloucester Vacation apartment rental

Cape Ann / Gloucester

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Glouce …see more

from $588 / night

$2,730 - $3,626 / week

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from $588 / night

13

Vacation b&b with golf nearby in Cape Ann

Cape Ann / Essex

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Our Bed & Breakfast is located in the small New England coastal town of Essex, MA. on Cape Ann. Historic farmhouse built in 1695 on 18 pristine areas of forest, fields and meadows. First free school in state. Front field used during Revolutionary War for militia traini …see more

from $150 / night

$1,050 / week

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from $150 / night

26

Home accommodation in Cape Ann

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

11

Vacation home in Cape Ann

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

17

Vacation home in Cape Ann

Cape Ann / Gloucester

5 13 2 nights min

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Child friendly
**There is a possibility that construction will ongoing near the property during the summer of 2016** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two …see more

from $429 / night

$3,003 / week

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from $429 / night

(3) Very Good 

26

Vacation apartment in Cape Ann

Cape Ann / Gloucester

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Private garden
UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a ve …see more

from $115 / night

$805 / week

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from $115 / night

(5) Excellent 

21

Vacation apartment in Cape Ann

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

$871 - $2,494 / week

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from $153 / night

(1) Excellent 

12

Cape Ann Vacation home rental

Cape Ann / Gloucester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 mi
  • Child friendly
  • Pet friendly
Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage h …see more

from $186 / night

$1,300 - $2,340 / week

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Responds fast!
avg. 3 hours 35 minutes

from $186 / night

(2) Very Good 

12

Vacation home in Cape Ann

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 49 minutes

from $175 / night

28

Cottage rental in Cape Ann

Cape Ann / Gloucester

7 12 Min stay varies

  • 7 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
Golden Sands is the quintessential turn of the century Gloucester beach "cottage." With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave this amazing beach hous …see more

from $1,010 / night

$5,005 - $7,180 / week

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from $1,010 / night

(2) Very Good 

12

Home rental in Cape Ann

Cape Ann / Gloucester

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Beach/lakeside relaxation
  • Ask about pets
This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is …see more

from $314 / night

$2,200 / week

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Responds fast!
avg. 3 hours 18 minutes

from $314 / 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 - $1,565 / week

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Responds fast!
avg. 41 minutes

from $169 / night

20

Cape Ann Vacation condo rental

Cape Ann / Rockport

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
Meet Me on South Street is a charming condo in a 2 unit antique colonial building that is one of Rockport's finest examples of Early American architecture. Lovingly and painstakingly renovated, this two-bedroom getaway is tastefully furnished and comfortable. A sunny pi …see more

from $280 / night

$1,380 - $1,845 / week

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from $280 / night

23

Vacation home in Cape Ann

Cape Ann / Gloucester

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Air conditioning
4 Bedrooms, 3 Baths (Sleeps 8) beautiful views, steps to private coffins beach Beautiful single family beach cottage, nestled among the pine trees, located on the private side of Wingaersheek Beach, which is well known as one of the most beautiful beaches on the North …see more

from $550 / night

$3,850 / week

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Responds fast!
avg. 9 minutes

from $550 / night

54

Vacation home in Gloucester

Cape Ann / Gloucester

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Air conditioning
Your Gloucester vacation experience awaits you in this spacious and versatile vacation home. Bell View can accommodate up to 16 people, making it the perfect getaway for family reunions or vacations with friends. The house was completely refurbished and refreshed in 201 …see more

from $970 / night

$4,830 - $6,630 / week

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from $970 / night

21

Vacation home rental

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Pet friendly
Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic "Gloucester Fisherman at the Wheel" sculpture -- a symbol of the fishing port's rich history as a working waterfront and …see more

from $280 / night

$1,280 - $1,755 / week

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from $280 / night

22

Vacation home in Cape Ann

Cape Ann / Rockport

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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 $772 / night

$4,030 - $4,690 / week

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from $772 / night

31

Vacation home in Cape Ann

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 - $3,380 / week

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from $559 / night