50 Best Cape Ann Vacation rentals on Holiday Lettings - Apartments

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185 Vacation rentals

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

$1,562 - $1,830 / week

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from $297 / 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 $89 / night

$623 / week

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Responds fast!
avg. 40 minutes

from $89 / 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

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

(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 this 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 beaches, this residence …see more

from $199 / night

$1,393 - $1,813 / week

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Responds fast!
avg. 22 minutes

from $199 / 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

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 $300 / night

$21,000 / week

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Responds fast!
avg. 12 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. Walk to Good Harbor Beach and scenic Back Shore. We call your home away from hom …see more

from $165 / night

$975 / week

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from $165 / night

31

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 ideally situated just 300 yards from the waterfront, as well as a short walk (1 mile) to a sandy beach, and the picturesque village of Rockport with its shops, restaurants, galleries and the world class Shalin Liu Performance Cente …see more

from $401 / night

$1,869 - $2,480 / week

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from $401 / 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

$2,073 - $2,780 / week

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from $442 / 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 $472 / night

$2,277 - $2,930 / week

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from $472 / 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 $241 / night

$1,103 - $1,777 / week

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from $241 / 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

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 $294 / night

$1,307 - $1,720 / week

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from $294 / 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 $588 / night

$2,686 - $3,575 / week

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from $588 / 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 48 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. 35 minutes

from $155 / night

23

Vacation home in Cape Ann

Cape Ann / Gloucester

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all …see more

from $572 / night

$2,788 - $3,580 / week

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from $572 / night

34

Gloucester Vacation home rental

Cape Ann / Gloucester

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Ask about children
Your family will love this extraordinary waterfront vacation rental home with spectacular views. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, views abound from almost every light-filled room. The house offers three levels of sophisticated, yet …see more

from $913 / night

$4,422 - $6,330 / week

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from $913 / night

(1) Excellent 

12

Apartment rental in Cape Ann

Cape Ann / Gloucester

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 1 mi
Enjoy your morning coffee and breathtaking sun rises on the covered porch, listen to the birds singing before you walk to Half Moon beach for a relaxing day at the ocean. Private entrance, dedicated parking spot on premise, fully equipped kitchen (with fridge, oven, s …see more

from $125 / night

$745 / week

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from $125 / night

(1) Excellent 

16

Home rental in Cape Ann

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 $297 / night

$1,435 - $1,895 / week

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from $297 / 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

(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

28

Vacation home in Cape Ann

Cape Ann / Rockport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Breathtakingly spectacular views from the living room and deck will keep you riveted to your lounge chair for most of your stay. The rest of the house is pretty amazing as well, with exquisite ocean views from just about every room. When you are ready to get up from yo …see more

from $1,155 / night

$6,669 - $7,030 / week

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from $1,155 / 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 $378 / night

$1,818 - $2,230 / week

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from $378 / night

24

Cape Ann Vacation home rental

Cape Ann / Gloucester

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Pet friendly
This immaculate beach house has it all: prime Good Harbor Beach location, views, historic charm and modern comfort and style. The original cottage was built as a stone carriage house to a neighboring estate. A wonderful octagonal addition has created a three bedroom/two …see more

from $670 / night

$3,248 - $4,380 / week

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from $670 / 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 $61 / night

$427 / week

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Responds fast!
avg. 44 minutes

from $61 / 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

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

$1,001 / week

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from $143 / 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

(2) Excellent 

18

Vacation cottage rental

Cape Ann / Rockport

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 $183 / night

$1,275 - $1,345 / week

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Responds fast!
avg. 45 minutes

from $183 / 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

20

Gloucester Vacation home rental

Cape Ann / Gloucester

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
A riverfront property on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets you will experience from the deck or the delightful gazebo. This home has a brand new …see more

from $547 / night

$2,686 - $3,455 / week

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from $547 / night

19

Cottage rental in Cape Ann

Cape Ann / Gloucester

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
Enjoy the views of the sparkling Annisquam River, lovely Wingaersheek Beach and the Annisqaum Yacht Club just across the river. You'll also be wowed by the incredible sunsets that await you every evening from this 3 bedroom/3.5 bath vacation rental home, which efficient …see more

from $472 / night

$2,277 - $3,030 / week

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from $472 / night

(17) Excellent 

26

Cottage rental in Gloucester

Cape Ann / Gloucester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Suitable for children age 5+
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 $230 / night

$1,800 / week

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Responds fast!
avg. 3 hours 23 minutes

from $230 / 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 immaculate 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- …see more

from $472 / night

$2,277 - $3,164 / week

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from $472 / night

17

Vacation home rental

Cape Ann / Gloucester

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Sun when you want it. Shade when you need it. Cool Cove is a beach house vacation rental that has it all! Sitting above Wingaersheek Beach, you will feel like you can see forever, enjoying views of Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, and sa …see more

from $1,280 / night

$6,006 - $8,230 / week

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from $1,280 / 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

$2,788 - $3,780 / week

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from $588 / 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

$1,307 - $1,845 / week

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from $330 / night

(5) Excellent 

17

Vacation home in Cape Ann

Cape Ann / Rockport

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min
  • 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