50 Best Vacation Rentals in Vineyard Haven - Holiday Lettings - Cabins

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1,233 Vacation rentals

31

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
Nestled in the lovely private community of homes and condos, this lovely two bedroom 2 and a half bath unit is just a five minute walk to the association pool and tennis courts and just two miles from Vineyard Haven Village Center. Relax on the large back deck with …see more

from $215 / night

$1,500 - $2,900 / week

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from $215 / night

17

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This newly renovated Cape is sure to please with A/C in every room, bamboo floors, new kitchen and baths. Great space and furnishings fresh and light throughout. Also includes a lower level family room. Large deck, enclosed outside shower and private spacious backyard. …see more

from $286 / night

$2,000 - $2,700 / week

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from $286 / night

17

Vacation home rental

Martha's Vineyard / Vineyard Haven

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Privately nestled atop a dune with breathtaking views and just steps from private swimming beach. This immaculate 2 bedroom, 1 bath beachfront cottage offers a tastefully furnished interior with sun filled rooms and panoramic views on both sides of the cottage.. Ste …see more

from $458 / night

$3,200 - $5,250 / week

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from $458 / night

31

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
In-town Classic Vineyard Home recently updated with central AC added in 2017. The outdoor living spaces are to be enjoyed by all, featured area a deck on one side offering outdoor patio dining and grill area and the screened porch on the opposite side of the house with …see more

from $443 / night

$3,100 - $3,900 / week

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from $443 / night

20

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Enjoy a view of Vineyard Haven harbor from most rooms of this 1898 Captain's home. The Captain Henry Stevenson house was recently renovated with stone countertops, stainless steel appliances, two flat screen TV's, central air and hardwood floors. Enjoy five large bedroo …see more

from $443 / night

$3,100 - $5,300 / week

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from $443 / night

22

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Families are sure to enjoy this custom designed home with open spaces and light filled rooms. Privately located yet a walk to town. There are three living spaces so guests can relax together or find a space to call your own. The main living level features a gourmet …see more

from $458 / night

$3,200 - $4,100 / week

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from $458 / night

17

Home rental in Vineyard Haven

Martha's Vineyard / Vineyard Haven

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
Enjoy expansive harbor views and passing tall masted schooners from the breezy wrap-around porch of this delightful five bedroom classic Vineyard home over the harbor. Stroll to the village center, tennis, fine and family dining, library, art galleries, and shopping. …see more

from $536 / night

$3,750 - $4,750 / week

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from $536 / night

30

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Gracious Beach Home. A spacious open floor plan with views from every room. First floor Master Suite opens to a wrap around deck. Small detached guest house with full bathroom. Private white sand beach. \n Amenities and Features include...\n \nWaterfront and Beachfront …see more

from $858 / night

$6,000 - $16,000 / week

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from $858 / night

23

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
Beautiful home in Mink Meadows area of West Chop. Guests will enjoy the gorgeous waterviews across Mink Meadows Pond to the North Shore, swans, geese and ducks reside in the pond a visual treat for all and the sunsets are breathtaking over the North Shore. Walk or dr …see more

from $429 / night

$3,000 - $6,250 / week

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from $429 / night

(1) Excellent 

28

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
Beautifully maintained four bedroom contemporary home in private North Shore location. Just a short walk or drive to the beach. This beach is great for walking and kayaking and can be sandy or rocky depending on seasonal storms. Large porch and deck, privacy yet less th …see more

from $429 / night

$3,000 - $3,750 / week

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from $429 / night

27

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Grand West Chop Home, designed to by a noted Vineyard Architect to highlight the magnificent water views. Surrounded by lush grounds and featuring an expansive bluestone patio, -a place to gather, dine, relax and take in the magnificent ocean views. The entry level f …see more

from $858 / night

$6,000 - $19,000 / week

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from $858 / night

40

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
A truly spectacular way to spend your time on the island of Martha's Vineyard. Enjoy the good life! Waterfront Lagoon: Gorgeous Contemporary with waterviews from just about every room. Spectacular lighting and a baby grand player piano draw you in, absolutely romant …see more

from $1,000 / night

$7,000 - $10,000 / week

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from $1,000 / night

25

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Air conditioning
This spacious waterfront home offers spectacular 180-degree Lagoon views, lagoon beach area perfect for launching kayaks and a great play beach area for children. This lovely home boasts all the amenities is just minutes away from the central town areas of Edgartown, Oa …see more

from $785 / night

$5,500 - $7,500 / week

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from $785 / night

15

Studio rental in Vineyard Haven with golf nearby

Martha's Vineyard / Vineyard Haven

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
FROG-Finished Room Over Garage for maximum, TWO(2) ADULTS ONLY. Not suitable for children. Located in a quiet residential neighborhood that is walking distance from the Vineyard Haven ferry, town, restaurants, shopping and beach. 2 night minimum. No Smoking, No Pets. OP …see more

from $225 / night

$1,575 / week

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from $225 / night

27

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Lagoon Front Luxury home, custom designed and built, craftsmanship visible throughout, floor to ceiling windows on the water side, open living spaces for your vacation enjoyment. This impeccable light filled home boasts beautiful water views of the lagoon from ju …see more

from $600 / night

$4,200 - $7,500 / week

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from $600 / night

22

Vacation home with swimming pool in Vineyard Haven

Martha's Vineyard / Vineyard Haven

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Contemporary design, this spacious home has just been updated and features two spacious living areas, 5 bedrooms and 3.5 bath. Designed to accommodate two families the lower level features a large family TV room, two bedrooms and a bath. The main living level has an upd …see more

from $500 / night

$3,500 - $8,000 / week

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from $500 / night

23

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
A 15 minute walk from Main Street and Vineyard Haven Ferry Terminal (as well as playground near by), makes this new construction, contemporary farmhouse a real gem! Relax in the hanging swing on the wrap-around farmer's porch and enjoy the peaceful vineyard pace. This r …see more

from $315 / night

$2,200 - $2,700 / week

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from $315 / night

25

Vacation home rental

Martha's Vineyard / Vineyard Haven

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
Upon entering this pristine clean cape, you are greeted by an open floor plan and light filled rooms. A double living area with multiple seating areas and TV, features lovely waterviews and opens to the deck and yard area. The spacious dining area is adjacent to the k …see more

from $315 / night

$2,200 - $3,500 / week

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from $315 / night

40

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Air conditioning
This luxury, in-town home was built by one of the island’s preeminent craftsmen and no expense was spared in creating the millwork details and sleek designer styling of the interior. The hand-crafted architectural detail includes reclaimed wood ceilings, unique cabinetr …see more

from $450 / night

$3,150 - $5,750 / week

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from $450 / night

25

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Air conditioning
Set in Tashmoo Woods an enclave of private homes and condominium units with association amenities,- pool and tennis courts just a short walk from the unit. This unit has a private deck with patio table, additional outdoor seating and grill. Upon entering this spacio …see more

from $286 / night

$2,000 - $2,600 / week

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from $286 / night

32

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
This elegant, charming waterfront home on the lagoon features beautiful views and a lovely landscaped yard. Families are sure to enjoy the pristine interior with open living space in the chef's kitchen, living and dining area, all of which open onto a spacious deck over …see more

from $929 / night

$6,500 / week

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from $929 / night

25

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Stunning Makonikey Contemporary: Completed in 2006, this fabulous home features gourmet kitchen, butler's pantry, wine cooler, professional cook stove, 2 ovens and 2 dishwashers. Large open family room with fireplace surrounded by windows and opens to deck and large lan …see more

from $529 / night

$3,700 - $8,000 / week

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from $529 / night

14

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Air conditioning
Adorable home located walking distance to downtown Vineyard Haven. Stroll down the hill after dinner and grab an ice cream cone for desert! Three bedrooms and one and a half bath home with tasteful furnishings. Lovely updated kitchen that flows into the dining room. E …see more

from $400 / night

$2,800 / week

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from $400 / night

9

Vacation studio in Vineyard Haven

Martha's Vineyard / Vineyard Haven

Studio 3 7 nights min

  • Studio
  • Sleeps 3
  • 7 nights min
  • Ask about children
  • Air conditioning
Perfectly cozy, this cute efficiency condo is situated just at the edge of town and is part of the Causeway, Harborview Complex. There is a common pool for when you are not at the beach, pay per wash laundry facilities at the complex and common picnic area on the ground …see more

from $115 / night

$800 - $1,050 / week

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from $115 / night

14

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This completely renovated in town house is just a 5 minute walk to town, restaurants, shopping, etc... Completely private back yard and deck. \n Amenities and Features include...\n \nIn Town, Central Air Conditioning …see more

from $286 / night

$2,000 - $3,700 / week

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from $286 / night

30

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Impeccably maintained 4 bedroom, 3 bath home located in the community of summer homes known as Tashmoo Cove. Featured association amenities include a large pool, tennis courts (as seen in the photos) and a dock on lake Tashmoo from which to launch Kayaks, 10 minute wal …see more

from $429 / night

$3,000 - $6,000 / week

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from $429 / night

18

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
MVVR Exclusive: Beautifully appointed with a mix of Asian and Tibetan antique furniture, furnishings from Napa Valley, Sundance and Pottery Barn, and original art work, this highly desirable townhouse provides a luxurious but comfortable setting for a memorable Vineyard …see more

from $254 / night

$1,775 - $3,175 / week

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from $254 / night

35

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Relax and enjoy the picturesque views of the outer harbor, with its plethora of boats going by each day, from the screened Gazebo, porch and patio areas. The wide, sandy private beach offers excellent swimming for both adults and children. The large yard with beautiful …see more

from $572 / night

$4,000 - $8,550 / week

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from $572 / night

20

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
Lovely antique Greek Revival at the edge of town on Main Street. This home offers four bedrooms with the two on the first being ensuite with full bathrooms. Nicely appointed with antiques, private off street parking with pleasant gardens, patio and yard. Walk to great …see more

from $586 / night

$4,100 - $6,500 / week

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from $586 / night

18

Vacation studio in Vineyard Haven

Martha's Vineyard / Vineyard Haven

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Ask about children
This lovely three bedroom home located on the beautiful waters of Tashmoo (tidal saltwater lake connecting to Vineyard Sound). The modern open floor plan, kitchen, living, dining with water views from every window is a great place for families to gather. The side patio …see more

from $1,072 / night

$7,500 / week

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from $1,072 / night

31

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Ask about children
  • Air conditioning
Newly updated water view home located within walking distance to downtown Vineyard Haven yet lots of privacy. Expansive decks one on the front of the house and one at the rear of the house and a screened in porch allow for outdoor entertaining, relaxing and enjoying th …see more

from $300 / night

$2,100 - $5,550 / week

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from $300 / night

21

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
A Beautifully designed and decorated comfortable home just one mile from downtown Vineyard Haven. Sweeping water views for the Master bedroom will have you entranced. The summer breezes provide a cooling caress. The many amenities offer solace during your much needed va …see more

from $714 / night

$5,000 - $19,000 / week

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from $714 / night

25

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

7 9 Min stay varies

  • 7 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
Come and enjoy this wonderful West Chop home! Step back in time to the simpler days on the island and enjoy this well-kept quintessential Vineyard Home. There are seven bedrooms allowing ample space for family and friends, the home sleeps 9. There is a traditional flo …see more

from $643 / night

$4,500 - $7,000 / week

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from $643 / night

24

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
Completely renovated Greek Revival home (the Berkshire House) on historic William Street with walking path one block from Main Street. Every inch of this home has been thoughtfully redone while maintaining much of the original detail and character. Small rooms have been …see more

from $843 / night

$5,900 - $9,900 / week

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from $843 / night

15

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
Beautiful, spacious contemporary home, just a short walk from the village of Vineyard Haven, Lagoon Pond and bike paths. This home is located on a private, wooded acreage with large fenced in yard, landscaped gardens, and hammock for relaxing. Features include a fully e …see more

from $286 / night

$2,000 - $3,000 / week

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from $286 / night

27

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This wonderful 4 bedroom, 3.5 bath home is located in the desirable West Chop. Walk to town. Lovely state of the art kitchen and spacious dining area open to a large deck. The wonderful family home has central A/C, ceiling fans in all bedrooms. An open living, kitch …see more

from $415 / night

$2,900 - $4,425 / week

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from $415 / night

14

Vineyard Haven Vacation home rental

Martha's Vineyard / Vineyard Haven

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
Delightful private summer retreat with magnificent beach rights just a 5 minute walk away. Open and airy pristine house complimented by a large deck. One and a half miles from town, close to Mink Meadows Golf Course. \n Amenities and Features include...\n \nShared priv …see more

from $429 / night

$3,000 / week

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from $429 / night

39

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Air conditioning
Exquisite waterfront family compound sleeps 12, with 270 degree waterview of the Lagoon, perfect private sandy on lagoon beach, private dock for boaters. Owner provides 2 kayaks! Larger boats, skiffs, paddle boards and various other water gear can rented and delivered t …see more

from $715 / night

$5,000 - $15,000 / week

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from $715 / night

35

Home rental in Vineyard Haven

Martha's Vineyard / Vineyard Haven

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Ask about children
Privacy, waterviews, walk to private beach. Kayak on scenic Aunt Rhoda's pond. Wonderful post and beam family compound. Sleeps 14. 6 bedrooms, 3.5 baths. An area of the Vineyard few will ever experience yet convenient to town, dining, theaters, golf, galleries, etc... …see more

from $458 / night

$3,200 - $5,700 / week

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from $458 / night

27

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

8 10 Min stay varies

  • 8 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
A very well maintained, charming, Vineyard Classic, with a wrap around porch on which you may recline, sip iced tea, and watch the yachts go by! a towel out of the towel basket on the porch, walk down the steps to the beach, sun yourself on the sand or jump in your kay …see more

from $1,429 / night

$10,000 - $13,500 / week

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from $1,429 / night