Sag Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Sag Harbor vacation rentals

Living area

Newly Renovated Sag Harbor Beach House with Pool

Newly Renovated Sag Harbor Beach House with Pool
Sag Harbor
The price is ￥42,232
￥106,342 total
includes taxes & fees
Mar 27 - Mar 28
Newly Renovated Sag Harbor Beach House with Pool
Interior

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
The price is ￥214,232
￥362,425 total
includes taxes & fees
Mar 29 - Mar 30
Sag Harbor Water View w Dock 1.5ml from town
Smart TV, fireplace

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is ￥634,760
￥1,021,464 total
includes taxes & fees
Mar 30 - Mar 31
Spacious 5-bedroom house with water views and 2 houses from the bay.
Interior

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is ￥35,705
￥59,588 total
includes taxes & fees
Apr 20 - Apr 21
Floating Nest on Private River. Serene Views & Ultimate Relaxation
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,308 reviews)
"Great property "
United States
brian
The price is ￥24,100
￥30,657 total
includes taxes & fees
Apr 15 - Apr 16
Montauk Manor
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is ￥23,523
￥31,191 total
includes taxes & fees
Apr 13 - Apr 14
Windward Shores Ocean Resort
Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is ￥25,043
￥28,612 total
includes taxes & fees
Apr 1 - Apr 2
North Fork Cottages & RV Resort
Apartment | Iron/ironing board, free WiFi

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (420 reviews)
"Great spot- walkable and nice accommodations! "
United States
Lesley
The price is ￥21,690
￥26,513 total
includes taxes & fees
Mar 31 - Apr 1
Montauk Oceanside Suites
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is ￥27,493
￥38,306 total
includes taxes & fees
Apr 2 - Apr 3
Cliffside Resort Condominiums
Beach nearby

The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very Good, (2 reviews)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
The price is ￥12,531
￥31,607 total
includes taxes & fees
Mar 29 - Mar 30
The Anchor at Soundview · Beach+Ocean+Sunrise
2 bedrooms, iron/ironing board, WiFi, bed sheets

#34- Stunning-Newly Remodeled

#34- Stunning-Newly Remodeled
Old Lyme
#34- Stunning-Newly Remodeled
Apartment | Living area

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (280 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is ￥34,277
￥47,791 total
includes taxes & fees
Apr 15 - Apr 16
The Surf Club
1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (38 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ￥15,567
￥31,844 total
includes taxes & fees
Apr 1 - Apr 2
1-bedroom cottage with Grove Beach 🏖️ access.
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is ￥87,121
￥117,665 total
includes taxes & fees
Mar 29 - Mar 30
Offshore Residences
Exterior detail

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Calverton
8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is ￥71,268
￥132,368 total
includes taxes & fees
Mar 30 - Mar 31
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥25,423
￥84,585 total
includes taxes & fees
Mar 30 - Mar 31
Beachside Bliss w/ Game Room, Gym & Golf Green
Exterior

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (43 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is ￥40,166
￥82,930 total
includes taxes & fees
Mar 31 - Apr 1
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Interior

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (136 reviews)
"This house was in a great location for our extended family Christmas gathering in Deep River. There was more than enough room for 3 adult couples and 2 older children tonstay comfortably & enjoy a cosy fire in fireplace one evening. "
United States
Karen B.
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sag Harbor Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Perfect "
Stephen 1-night trip
Posted 3 hours ago
The Harbor Front Inn

Find out more about Sag Harbor

Search for holiday rentals in Sag Harbor on Expedia! You can easily find your home rentals, villas, holiday apartments in Sag Harbor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Sag Harbor!

Frequently asked questions

Can I find a vacation rental in Sag Harbor?

Yes, we give you a choice of vacation rentals in Sag Harbor close to Bay Street Theatre, or you can go with a more secluded option if you want a relaxing stay. Discover why Sag Harbor is known for its waterfront. Make sure you have time to check out the beaches and churches during your trip.

What are some of the best vacation home rentals that Sag Harbor has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : You might like this vacation home rental near Sag Harbor. It is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Sag Harbor?

With 304 Expedia vacation rentals, you're sure to find just the right place for your Sag Harbor stay.

What can I see and do in Sag Harbor?

Cultural attractions include Bay Street Theatre and Sag Harbor Whaling and Historical Museum, whereas Foster Memorial Town Beach and The Hamptons Beaches are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Havens Beach and Noyac Golf Club.

What are vacation rentals like in Sag Harbor?

Vacation rentals are private properties you can book for several days or longer in Sag Harbor. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for families.