50 Best Cape Ann Vacation rentals on Holiday Lettings - Apartments

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Cape Ann

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182 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

20

Gloucester Vacation apartment rental

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both …see more

from $230 / night

$1,080 - $1,777 / week

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from $230 / 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 $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

(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 $150 / night

$1,000 - $1,900 / week

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from $150 / night

21

Vacation home in Cape Ann

Cape Ann / Gloucester

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
Enjoy the ambiance of Victorian Gloucester with all the amenities of the 21st century from this classic period vacation rental home, which is tastefully decorated with the traveler in mind. Enter the house through the front door and enjoy two parlors--one with a large b …see more

from $545 / night

$2,705 - $3,575 / week

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from $545 / 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 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

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

(30) 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

(1) Excellent 

17

Home rental in Gloucester

Cape Ann / Gloucester

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Ask about children
Welcome, cher ami ("dear friend"), to this gleaming second-floor vacation rental. Cher Ami is available as a summer rental and an off-season rental. Cher Ami is a spacious and sunny apartment, with 2 bedrooms plus an office space, an eat-in kitchen with an island, 2 …see more

from $160 / night

$1,115 - $1,215 / week

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from $160 / 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

25

Vacation home in Cape Ann

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

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 $91 / night

$637 / week

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Responds fast!
avg. 21 minutes

from $91 / 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

(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

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

(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 48 minutes

from $160 / 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 - $1,720 / week

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from $280 / night

21

Vacation home in Cape Ann

Cape Ann / Gloucester

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This delightful 3 bedroom, 1.5 bath Queen Anne-style vacation rental home is bright and cheery and just waiting for you! Enter the house into the kitchen from the verdant and sizable back yard (or choose one of the other 2 doors). The sunny kitchen has plenty of stor …see more

from $330 / night

$1,280 - $1,845 / week

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from $330 / 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 - $3,680 / week

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from $588 / night

(2) Excellent 

18

Vacation cottage in Cape Ann

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

(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 - $1,813 / week

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Responds fast!
avg. 15 minutes

from $199 / night

(17) Excellent 

26

Cottage rental in Gloucester

Cape Ann / Gloucester

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large pri …see more

from $240 / night

$1,860 - $2,000 / week

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Responds fast!
avg. 3 hours 4 minutes

from $240 / night

28

Home rental in Gloucester

Cape Ann / Gloucester

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Enjoy a coastal retreat when you stay at this one-bedroom apartment in Gloucester. Complete with stunning ocean views and a great location near several beaches, this unit has modern amenities inside, along with a lovely patio and outdoor grill. Located in Gloucester, …see more

from $65 / night

$455 / week

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Responds fast!
avg. 21 minutes

from $65 / night

31

Vacation home rental

Cape Ann / Gloucester

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly
Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2.5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious su …see more

from $672 / night

$2,930 - $4,243 / week

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from $672 / night

23

Vacation home in Cape Ann

Cape Ann / Gloucester

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $300 / night

$21,000 / week

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Responds fast!
avg. 11 minutes

from $300 / 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

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 55 minutes

from $250 / night

(9) 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

$840 - $1,512 / week

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Responds fast!
avg. 3 hours 13 minutes

from $110 / 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 Cape Ann

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

(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

20

Vacation cottage in Cape Ann

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

23

Gloucester Vacation home rental

Cape Ann / Gloucester

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Ask about children
Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scenic Gloucester Harbor. Nestled close to the shore, vistas abound from its ample deck and most interior rooms. The view of sailboats, Gloucester’s fable …see more

from $650 / night

$3,230 - $4,330 / week

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from $650 / 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 - $3,405 / week

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from $559 / night

33

Vacation home in Cape Ann

Cape Ann / Gloucester

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Direct waterfront on picturesque Goose Cove, this vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, …see more

from $450 / night

$2,230 - $3,080 / week

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from $450 / night

(3) Excellent 

15

Vacation b&b in Cape Ann

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 Cape Ann

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

(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 13 minutes

from $186 / night