50 Best Sag Harbor Vacation rentals on Holiday Lettings - Condos

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57 Vacation rentals

17

Cottage rental in Sag Harbor

Hamptons / Sag Harbor

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Wonderful Sag Harbor VillageWaterfront Cottage for Rent 3 bedrooms, 4 queen size beds , 1 1/2 baths, A/C, Screaming Water views, multi level Decks, Private Sand beach, with Kayaks and fire pit. All inclusive utilities, Maid service (weekly) and wonderful clear Water …see more

from $900 / night

$6000 / week

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Responds fast!
avg. 3 hours 55 minutes

from $900 / night

(4) Excellent 

11

Vacation b&b in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Suitable for children age 5+
This whaling captain's house has been in my family six generations. We offer the original wing of house for weekend rental May through October. Each bedroom has a water view, and they share a dressing room/office. Enjoy the spacious porch, that includes an eating ar …see more

from $275 / night

$1701 - $2750 / week

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from $275 / night

(4) Excellent 

28

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is 2 weeks during High Season unless you see an availability between rentals. During the off season 1 week rentals may be possible. This elegan …see more

from $2143 / night

$15000 - $19000 / week

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Responds fast!
avg. 2 hours 40 minutes

from $2143 / night

6

Home rental in Sag Harbor

Hamptons / Sag Harbor

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
This beach vibes cottage is located in Sag Harbor village, you can walk to town, bike or walk to the beach. The house is located in the only private beach community in Sag Harbor. The cottage comes fully furnished with everything you need to have a memorable stay in Sag …see more

from $350 / night

$2450 / week

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from $350 / night

(1) Good 

12

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The Sea Breeze House is located in the enchanting community of Sag Harbor. The house is located just steps from the only private beach in the Hampton. You can walk or bike to town. Watch the sunset from the front porch, enjoy the evening sea breeze. The Space: The Se …see more

from $950 / night

$6650 / week

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from $950 / night

(4) Excellent 

21

Vacation apartment rental

Hamptons / Sag Harbor

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
From its commanding position on Main Street in the heart of Sag Harbor village, this spectacular vintage Victorian is an authentic testament to the history of Sag Harbor. With distinctive architecture and classic styling, the impressive house features the Upstairs Apart …see more

from $495 / night

$2600 - $2950 / week

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Responds fast!
avg. 1 hour 47 minutes

from $495 / night

(2) Excellent 

14

Vacation b&b in Sag Harbor

Hamptons / Sag Harbor

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Suitable for children age 5+
Historic whaling captains home. We are the sixth generation to live here. It is a quick walk from our house to the village of Sag Harbor, where you will find restaurants, boutiques, antique stores, marinas and much more. If you wish to stay around the house, we have …see more

from $475 / night

$3000 - $4575 / week

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from $475 / night

11

Vacation home in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets
Perfect get away in the heart of the village. Newly renovated carriage house in the historic district. 2 bedrooms, kitchen, dining room, living room, full bathroom, private yard. Located in the Historic District of Sag Harbor Village. Only 10 minutes walk to the cente …see more

from $600 / night

$3000 / week

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from $600 / night

24

Home rental in Sag Harbor

Hamptons / Sag Harbor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Escape from reality in this charming 2-bed, 2-bath Sag Harbor house, which sleeps up to 6. Located just minutes from a private beach, restaurants and shopping, this darling abode is the ideal destination for those looking to explore the Hamptons! You’ll know you made t …see more

from $449 / night

$3143 - $6293 / week

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from $449 / night

8

Vacation home in Sag Harbor

Hamptons / Sag Harbor

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
Spacious 1700's Traditional on "Captains Row" in Historic Sag Harbor. Recently renovated to include cathedral ceiling bedroom and bath with rear entrance. Five minutes to downtown shops, 10 minutes to Sag Harbor Cove. Antique furnishings, 3 decorative fireplaces, one ga …see more

from $457 / night

$3199 - $3839 / week

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from $457 / night

30

Vacation home in Sag Harbor

Hamptons / Sag Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0.001 mi
  • Child friendly
Resort style living in this fantastic private beachfront oasis in Sag Harbor Village. Enjoy fabulous views and amazing sunsets over Sag Harbor Bay from this wonderful 3 bedroom, 2.5 bath house with hot tub and sandy beach right in your backyard. Great family rental. K …see more

from $1500 / night

$8500 - $10000 / week

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from $1500 / night

7

Home rental in Sag Harbor

Hamptons / Sag Harbor

6 12 30 nights min

  • 6 bedrooms
  • Sleeps 12
  • 30 nights min
  • Child friendly
  • Ask about pets
OPEN HOUSE!! Sunday May 18 One of the last houses in the area with pool AND tennis! MD-LD $60,000 Please call first. Welcome to my paradise! My home has everything you need for a fantastic summer. 6 bedroom/4 bath contemporary home on 10 secluded acres. Heated in ground …see more

from $1000 / night

$7000 / week

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from $1000 / night

15

Vacation home in Sag Harbor

Hamptons / Sag Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This stunning, spacious three bedroom home, with water views from every room, and a heated gunite pool, will be your dream-come-true vacation rental. You will be minutes away from several gorgeous beaches as well as 1 mile from the lively and historic village of Sag …see more

from $795 / night

$7500 / week

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from $795 / night

11

Vacation home in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This is a newly renovated bungalow with 2 bedrooms, full living room, eat-in kitchen, closed in and sunny porch, roomie deck with outdoor furniture (in season). It is a 5-10 minute walk to the village, fine restaurants, museums, shops, churches and temple and beach.Th …see more

from $300 / night

$1500 - $2200 / week

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from $300 / night

26

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

6 12 6 nights min

  • 6 bedrooms
  • Sleeps 12
  • 6 nights min
  • Child friendly
This home sits on 2.2 private and gated acres surrounded by nature. Viking kitchen, double sinks, double dishwashers and wine cooler. Six well appointed bedrooms, 3 en-suite. Three fireplaces. Formal living room, den, outdoor den, outdoor living room, formal dining roo …see more

from $3000 / night

$18000 / week

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from $3000 / night

(4) Excellent 

10

Vacation cottage in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The ow …see more

from $500 / night

$3500 / week

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from $500 / night

21

Vacation home in Sag Harbor

Hamptons / Sag Harbor

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
Put up your feet and relax in this idyllic home just minutes from Long Beach and the rest of the luxuries the Hamptons have to offer. The open concept kitchen is a chef's dream, with a six burner Viking stove, Subzero refrigerator, Bosch dishwasher, and plenty counter …see more

from $780 / night

$5000 / week

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from $780 / night

(1) Excellent 

16

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Privately situated on a park-like landscaped grounds, this classic 2 story French cottage was completely renovated for modern comfort and indoor/outdoor summer entertainment. This delightful house features an open-plan living room with fireplace, dining room, a gourme …see more

from $695 / night

$4865 / week

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from $695 / night

16

Sag Harbor Vacation villa rental

Hamptons / Sag Harbor

10 16 4 nights min

  • 10 bedrooms
  • Sleeps 16
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Spectacular 13,000 square foot estate, on 30 acres of open reserve with water views, boasts 11 bedrooms, 13 full bathroom, heated gunite pool, large outside patio area, Grill, perfect for entertaining, weddings, large family gatherings, etc. Located in Bridgehampton nei …see more

from $3500 / night

$24500 - $42000 / week

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from $3500 / night

24

Vacation home with swimming pool in Sag Harbor

Hamptons / Sag Harbor

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
It's like getting a free house! Generous lot bordering golf course has room for a substantial house, pool and tennis court. Presently improved with an easygoing modern home bordering Noyac Golf Club, with updated kitchen and baths, boasting a free-flowing floor plan, op …see more

from $1000 / night

$7000 / week

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from $1000 / night

9

Vacation cottage in Sag Harbor

Hamptons / Sag Harbor

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
  • Pet friendly
Lovely Village location, 3 bed 2 bath summer rental. Spend your summer in one of the best vil …see more

from $326 / night

$2282 - $2738 / week

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from $326 / night

30

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
On a quiet shy acre beautiful parcel sits this updated light filled home in a Development with wide street for walking. With 4 Master Ensuite bedrooms, spacious with 2 masters with king beds and private baths, one with queen bed and private baths and the other with two …see more

from $1750 / night

$9000 / week

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from $1750 / night

10

Vacation cottage rental

Hamptons / Sag Harbor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Enjoy this Newly Renovated 3 Bedroom, 2 Bath Home with Hot Tub an …see more

from $393 / night

$2744 - $3293 / week

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from $393 / night

18

Vacation home rental

Hamptons / Sag Harbor

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
The feeling of Zen surrounds you as you enter upon this European designer's hideaway..Custom appointments of quality and luxury fill this Hampton's home. Located 12 minutes walk to Main Street of the prestigious Sag Harbor Village....0.4 acres of beautifully manicured t …see more

from $1667 / night

$11667 / week

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from $1667 / night

12

Vacation home in Sag Harbor

Hamptons / Sag Harbor

4 9 3 nights min

  • 4 bedrooms
  • Sleeps 9
  • 3 nights min
  • Child friendly
The Sea Breeze House is located in the enchanting community of Sag Harbor. The house is located walking distance to the only private beach in the Hamptons. You can walk or bike to town. Grab a bottle of wine head to the beach and enjoy the amazing sunset on the east end …see more

from $1000 / night

$7000 / week

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from $1000 / night

10

Apartment rental in Sag Harbor with swimming pool

Hamptons / Sag Harbor

1 8 30 nights min

  • 1 bedroom
  • Sleeps 8
  • 30 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning
Located in the quaint historic whaling Village of Sag Harbor, 12 minute walking distance to the center of town, with close proximity to the bay and ocean beaches. This European designer's home totals 5000 sq.ft., the lower level just shy of 1000, sq ft and is the desig …see more

from $1834 / night

$12834 / week

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from $1834 / night

16

Vacation home in Sag Harbor

Hamptons / Sag Harbor

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
Enjoy this 3 Bedroom, 2.5 Bath Immaculate Home near the Village in Sag Harbo …see more

from $587 / night

$4109 - $5136 / week

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from $587 / night

9

Vacation cottage in Sag Harbor

Hamptons / Sag Harbor

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Child friendly
This renovated charming and chic two bedroom beach cottage has every amenity you need to have a great summer right near the best bay beaches. Open and bright living space with gas fireplace, built in flat screen and central air. New open kitchen with stainless appliance …see more

from $386 / night

$2695 - $3234 / week

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from $386 / night

23

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Recently renovated four bedroom, three bath traditional house is located close to Sag Harbor Village. The home is tucked away in a quiet neighborhood within close proximity to Sag Harbor bay beaches and village. It features new kitchen, wide plank …see more

from $515 / night

$3605 - $4326 / week

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from $515 / night

15

Vacation guest house in Sag Harbor

Hamptons / Sag Harbor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 0.3 mi
  • Child friendly
  • Air conditioning
This beautiful, new space is nicely appointed with modern fixtures and finishes. High ceilings, clean and bright. Walk to the bay beach for stunning sunsets. New furniture, linens, towels, etc. Contact us for weekly, monthly or seasonal pricing. This beautiful, new …see more

from $250 / night

$1400 - $2520 / week

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from $250 / night

6

Sag Harbor Vacation apartment rental

Hamptons / Sag Harbor

1 2 14 nights min

  • 1 bedroom
  • Sleeps 2
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Great Suite available for your Summer Enjoyment. This is an Apartment Within a Larger Home. Perfect as a weekend Getaway for 2. Five minutes to Sag harbor, Five Minutes to Bridgehampton. Eight minutes to the Ocean.Hamptons Classic 5 Minutes away. Crisp and clean with yo …see more

from $197 / night

$1372 - $1715 / week

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from $197 / night

16

Vacation home in Sag Harbor

Hamptons / Sag Harbor

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Recently renovated chrisp and clean Sag Harbor charming home. Everything you would need for an Excellent Summer!!! Just a little over a mile from the center of the Village and just a skip to Long Beach to boot. Come home from a day at the Ocean 8 minutes away and relax …see more

from $522 / night

$3654 - $4568 / week

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from $522 / night

14

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Child friendly
This luxurious house has everything you need for a relaxing vacation. The ample sized lot backs onto a reserve, so your quiet is rest-assured. The entire house is tastefully furnished and cared for. It features a great room with fireplace, a huge eat in kitchen, a forma …see more

from $1435 / night

$10045 - $12054 / week

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from $1435 / night

4

Vacation apartment with shared pool in Sag Harbor

Hamptons / Sag Harbor

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Two bed, two bath first floor apartment that is seconds away from Long Beach, Bridge Golf Club, Sag Harbor Village and Bridgehampton. Be close to all the opportunities that the Hamptons have …see more

from $313 / night

$2191 - $2629 / week

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from $313 / night

23

Vacation home in Sag Harbor

Hamptons / Sag Harbor

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy this Beautifully Renovated 5 Bedroom, 2.5 Bath Home with Open Living/Dining Area, Finished Basement and Heated Pool. Finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely out …see more

from $1239 / night

$8673 - $10408 / week

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from $1239 / night

12

Sag Harbor Vacation cottage rental

Hamptons / Sag Harbor

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Child friendly
  • Air conditioning
Adorable, centrally air-conditioned, village cottage with an arbor covered deck, new kitchen, two bedrooms, one bath, two flagstone patios, nice garden, hammock and perfect for entertaining. Tasteful …see more

from $261 / night

$1827 - $2192 / week

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from $261 / night

4

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
An immaculate 3 bedroom, 2 bath, traditional Salt Box. Close to the village of Sag Harbor. Beautifully flowering gardens with numerous paths to different seating meditation areas and Round Pond. Completely new deck around house. Full walk-out basement with won …see more

from $391 / night

$2737 - $3284 / week

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avg. 1 minutes

from $391 / night

5

Vacation home rental

Hamptons / Sag Harbor

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Child friendly
Idyllic location on private lane with water views. Custom built with all top of the line amenities including bamboo floors throughout, gourmet chef's kitchen, huge living room with soaring ceiling and fireplace, elegant dining area. Great room and media room. There are …see more

from $1630 / night

$11410 - $13693 / week

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from $1630 / night

11

Vacation home rental

Hamptons / Sag Harbor

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
A cozy ranch with newly renovated kitchen and bath, features an alcove breakfast area that overlooks the heated pool and gardens; two guest bedrooms; master bedroom, and family room that opens out to the pool and gardens. The screened in porch enhances those summer nigh …see more

from $489 / night

$3424 - $4108 / week

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avg. 1 minutes

from $489 / night

7

Vacation home rental

Hamptons / Sag Harbor

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
This bayfront beach cottage has spectacular waterviews relax in the comfortable hammock the home has 3beds 2 baths the oerfectlocation to enjoy your summer on the water great deck for summer fun and inside theres a piano so u can sing your favorite tune,minutes to …see more

from $652 / night

$4564 - $5477 / week

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from $652 / night

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