50 Best Cape Ann Vacation rentals on Holiday Lettings - Apartments

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Cape Ann

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149 Vacation rentals

37

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 $550 / night

$513 - $3500 / week

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from $550 / 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 $139 / night

$973 / week

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from $139 / night

15

Vacation home in Cape Ann

Cape Ann / Rockport

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
New in 2017! Ideally situated just a short stroll from Old Garden Beach and the historic and quaint oceanfront village of Rockport, Beach Bound is a delightful and newly constructed 4 bedroom, 2.5 bath vacation home. Relax on the lovely back deck enjoying the home’s ser …see more

from $640 / night

$3200 - $3500 / week

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from $640 / 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
New in 2017! 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 w …see more

from $583 / night

$2600 - $3560 / week

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from $583 / night

29

Home accommodation in Cape Ann

Cape Ann / Essex

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
Available for rentals year round, Clamshell Landing is perfect for family vacations, family reunions, wedding accommodations, corporate outings or other events. This one-of-a-kind vacation rental home is perfect for sports enthusiasts or nature lovers and is complete wi …see more

from $1400 / night

$6600 - $8800 / week

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from $1400 / night

26

Home rental in Rockport

Cape Ann / Rockport

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
This lovely 3 bedroom vacation home is appointed with high end appliances, finishes and furnishings while remaining very comfortable and accommodating inside and out. The house is located in the sought-after Marmion Way location which offers the ultimate Rockport experi …see more

from $567 / night

$450 - $3500 / week

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from $567 / night

(16) Excellent 

26

Cottage rental in Gloucester

Cape Ann / Gloucester

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • 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 $250 / night

$1600 - $1960 / week

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Responds fast!
avg. 3 hours 28 minutes

from $250 / 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 $220 / night

$299 - $1600 / week

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from $220 / 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 $440 / night

$2175 - $3000 / week

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from $440 / 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 $283 / night

$1375 - $1815 / week

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from $283 / night

(10) Excellent 

25

Cape Ann Vacation home rental

Cape Ann / Gloucester

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Spacious 5 Bedroom Brick Colonial Home located on the Historic Stacey Boulevard with picturesque views of Gloucester's Harbor and the Atlantic Ocean. Look out at the stunning views of local schooners, the light houses, fishing vessels and feel the cool sea breeze that …see more

from $325 / night

$2200 - $2600 / week

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from $325 / night

34

Gloucester Vacation home rental

Cape Ann / Gloucester

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $750 / night

$3750 - $6204 / week

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from $750 / night

16

Cottage rental in Cape Ann

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 $220 / night

$1100 - $1450 / week

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from $220 / night

16

Cape Ann Vacation condo rental

Cape Ann / Manchester-by-the-Sea

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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

$1600 - $1845 / week

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Responds fast!
avg. 2 hours 41 minutes

from $250 / night

28

Vacation home in Cape Ann

Cape Ann / Rockport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
New in 2017! 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 g …see more

from $1150 / night

$6501 - $7018 / week

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from $1150 / 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

$800 - $1200 / week

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from $143 / night

29

Vacation home rental

Cape Ann / Rockport

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Boasting stunning views only imaginable from a home with direct water frontage, Spindrift, a 4+ bedroom, 2+ bath vacation rental home is located in Rockport’s lovely South End. It is the perfect location for rest and relaxation. According to the Oxford English Dictio …see more

from $750 / night

$4500 - $4578 / week

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from $750 / 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 $330 / night

$1400 - $2100 / week

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from $330 / night

35

Home rental in Cape Ann

Cape Ann / Rockport

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
This immaculate 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 …see more

from $850 / night

$3750 - $5188 / week

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from $850 / night

(5) Excellent 

21

Vacation apartment in Cape Ann

Cape Ann / Rockport

2 7 2 nights min

  • 2 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Built in 1900, this classic New England beach house is located in the Headlands neighborhood in Rockport, Massachusetts. Steps away is the charming Old Garden Beach, secluded enough to remain a hidden jewel of Rockport. Also a short walk away is the Headlands, providing …see more

from $199 / night

$999 - $2494 / week

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from $199 / night

25

Vacation home in Cape Ann

Cape Ann / Essex

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
Life is a voyage, and Way Point is the perfect place to launch part of your voyage. Way Point is not only the name of this adorable two bedroom vacation rental apartment, it also refers to a nautical sailing term which means "a stop along the way, or a place to change c …see more

from $150 / night

$350 - $1150 / week

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from $150 / night

33

Vacation home in Cape Ann

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Pet friendly
Rockport oceanfront! This sunny and immaculate 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, …see more

from $667 / night

$3200 - $4400 / week

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from $667 / night

23

Rockport Vacation cottage rental

Cape Ann / Rockport

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This sweet 2 bedroom vacation rental cottage is the perfect place to be this summer, as it is all about the sun, sand and surf of wonderful mile long - Long Beach, which is just about 25 yards from the cottage. The cottage is all on one level, with a wonderful sun po …see more

from $186 / night

$1300 - $1750 / week

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from $186 / night

33

Vacation home in Cape Ann

Cape Ann / Gloucester

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $450 / night

$488 - $3050 / week

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from $450 / 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

$3651 / week

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from $400 / 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, MA …see more

from $99 / night

$693 / week

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from $99 / night

32

Vacation home in Cape Ann

Cape Ann / Rockport

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This waterfront historic vacation home is centrally located in the village of Rockport and was home to John Oakes in the late 18th and early 19th centuries. Completely renovated in 2015 and brought up to the highest modern standard, it retains its old world charm. It ha …see more

from $403 / night

$2815 - $3764 / week

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from $403 / night

40

Vacation home in Cape Ann

Cape Ann / Gloucester

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Pet friendly
Located above the western shore of Gloucester’s historic harbor and lovingly renovated in 2011, this beautiful and spacious five bedroom Victorian vacation rental home has been in the same family since the 1880's. This gracious home gives hints to a bygone era while …see more

from $470 / night

$2350 - $3052 / week

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from $470 / 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 $546 / night

$2400 - $3400 / week

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from $546 / night

(3) Very Good 

26

Vacation apartment in Cape Ann

Cape Ann / Gloucester

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 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

25

Vacation home in Cape Ann

Cape Ann / Rockport

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
New in 2016! 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 t …see more

from $300 / night

$1650 - $2300 / week

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from $300 / 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

$1275 - $1346 / week

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Responds fast!
avg. 51 minutes

from $183 / 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 $583 / night

$2700 - $3651 / week

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from $583 / night

20

Home rental in Cape Ann

Cape Ann / Gloucester

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly
This large, comfortable family-oriented vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the gro …see more

from $538 / night

$2600 - $3550 / week

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from $538 / night

(27) Excellent 

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
PERIWINKLE COTTAGE - truly a place to call "a home away from home". This 2-unit, townhouse cottage offers guests privacy and an updated seaside decor with today's modern amenities. (You can only reserve Unit #1 on this site). UNIT #1; --Unfortunately, we are NOT able …see more

from $125 / night

$875 - $1050 / week

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from $125 / night

36

Cape Ann Vacation home rental

Cape Ann / Rockport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
This waterfront vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor with unobstructed 180 degree views of the Atlantic, Sandy Bay, and the twinkling lights of the village of Rockport. The location of the home is ideal, away from all the hustle of to …see more

from $730 / night

$3651 - $5225 / week

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from $730 / 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

$3850 / week

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from $550 / night

22

Vacation home rental

Cape Ann / Rockport

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • 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 $438 / night

$2000 - $2750 / week

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from $438 / night

33

Cape Ann Vacation home rental

Cape Ann / Gloucester

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Rosemarc House has stairs that take you directly onto the private portion of Good Harbor Beach. This immaculate 3 bedroom, 3.5 bath luxury vacation rental home is the ultimate beach getaway. Incredible 180 degree views of the whole length of the beach, Salt Island and …see more

from $929 / night

$6501 - $10128 / week

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from $929 / 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 $320 / night

$400 - $1815 / week

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from $320 / night