25 Best Sag Harbor Vacation rentals on Holiday Lettings - Condos

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29 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

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

(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 41 minutes

from $495 / night

(6) 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

$1700 - $2750 / week

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from $275 / 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

(5) 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. 3 hours 0 minutes

from $2143 / 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 / week

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from $1500 / night

(3) Very Good 

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

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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Responds fast!
avg. 3 hours 3 minutes

from $250 / 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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Responds fast!
avg. 3 hours 45 minutes

from $695 / 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

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

24

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Child friendly
We have remodeled our 2,000 square foot home. It is a bright, airy, inviting space where you can relax outside on the patio or enjoy family and friends inside in one of our many open living spaces. During the day you can drive down to our private beach, play a few hol …see more

from $550 / night

$3750 / week

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from $550 / 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

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

6

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

6 20 2 nights min

  • 6 bedrooms
  • Sleeps 20
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This Spacious Contemporary home is great for entertaining and play. The interior kitchen/dining is open and light filled. There are 2 living rooms and 2 dining areas as well as a breakfast bar. There are sliding glass doors to the large deck which affords flow be …see more

from $1750 / night

$4000 - $6800 / week

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from $1750 / 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

19

Vacation home in Sag Harbor

Hamptons / Sag Harbor

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool
On a quiet shy 2 acre beautiful parcel adjacent to hundreds of acres of town reserve sits this updated light filled home with sweeping lawn, and reserves on 3 sides for complete privacy. Spacious with 4 bedrooms and 3.5 baths,Two masters with king beds and private baths …see more

from $1750 / night

$8500 - $10250 / week

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from $1750 / 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

21

Vacation home in Sag Harbor

Hamptons / Sag Harbor

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
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

19

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Child friendly
This property has just gone through a hi-end renovation. It has a beautiful updated Viking kitchen, amazing yard with a 50 ft gunite pool with shallow end "tanning bed", great for kids and adults alike! There are four bedrooms, 3 full baths in the main house, plus an …see more

from $2000 / night

$11000 / week

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from $2000 / 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

39

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

4 10 90 nights min

  • 4 bedrooms
  • Sleeps 10
  • 90 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Hello, This is a wonderful beach house to stay over the summer. It has everything you want in it (Salt Water Pool, Wreck Room, Jacuzzi, Home Theater, Alarm Systems, etc...)! For those who want the best, come here. It has wonderful views of beaches. In under 100 ya …see more

from $850 / night

$5950 / week

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from $850 / night

24

Vacation villa with swimming pool in Sag Harbor

Hamptons / Sag Harbor

5 10 14 nights min

  • 5 bedrooms
  • Sleeps 10
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This villa features 5,600 +/- sq. ft. of living space with five bedrooms, four and one-half baths, plus a gourmet kitchen, living room with fireplace, media room, office, large master, and a finished lower level, on 1.87 +/- beautifully landscaped ac. Located in The Ham …see more

from $3000 / night

$21000 - $31500 / week

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from $3000 / 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

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

13

Vacation home in Sag Harbor

Hamptons / Sag Harbor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abun …see more

from $725 / night

$4350 / week

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from $725 / night

7

Sag Harbor Vacation home rental

Hamptons / Sag Harbor

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Village traditional on a quiet village street perfect for family gatherings. Magnificent backyard including a stone patio with fridge, grill, heated gunite pool and beautiful gardens. The park is accessible from our backyard allowing children to enjoy fields and pla …see more

from $1115 / night

$7800 / week

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from $1115 / night