Fishers Island Holiday Rentals

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Holiday Rentals in Fishers Island

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1023)
"Best affordable hotel in Montauk"
The price is NZ$590
includes taxes & fees
3 Jun - 4 Jun
Montauk Manor
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (299)
"It was so close to town!"
The price is NZ$356
includes taxes & fees
5 Jun - 6 Jun
Montauk Oceanside Suites
The Surf Club
3.5 star property
8.4 out of 10, Very good, (220)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is NZ$527
includes taxes & fees
17 Jun - 18 Jun
The Surf Club
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Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (237)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is NZ$486
includes taxes & fees
3 Jun - 4 Jun
Windward Shores Ocean Resort
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (187)
"Such a nice weekend getaway. We probably rented the smallest of the rooms but it was still comfortable and accommodating. Had a mini kitchen that was perfect for us. ALL the staff were so friendly and helpful. I enjoyed the communications through text to set up room service and beach chairs for the next day. The heated pool was an absolute plus and so was the pool playing by the pool. Made us feel like we were away on an all inclusive vacation. "
The price is NZ$335
includes taxes & fees
2 Jun - 3 Jun
Driftwood Resort
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (73)
"We had the best time at Rick’s house in the Hamptons! We’d love to come back!"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, (11)
"Our floors were being refinished so we needed a place to stay for a week with our dog. The cottage was perfect for our needs, with plenty of space to walk our dog."
Private Guest House w/ Deck + Spectacular Views!
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (91)
"Had great time at property. Very close to town and beach. Would highly recommend."
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (63)
"Pictures don’t do it justice! So relaxing. Quiet and clean. Best we could ask for. The deck is great. It was bit cold so we couldn’t use the pool but we would love to be back for the summer! Very close to close to everything but still extremely quiet. Kelly was also an amazing host. She responded quickly and assisted with a parking question we had. Couldn’t ask for anything more. 5 stars!"
Newly Renovated Montauk Condo with Ocean Views!
Misquamicut Westerly Secluded Beach Cottage 2020 remodeled and upgraded.
9.8 out of 10, Exceptional, (152)
"Great time. Nice visit. Cottage was clean, very comfortable and as advertised. Would definitely stay again."
Misquamicut Westerly Secluded Beach Cottage 2020 remodeled and upgraded.
Lakeside cottage overhanging the water, beautiful window views across the lake
9.6 out of 10, Exceptional, (173)
"We went to Foxwoods for a concert and the rooms there were ridiculously priced. I ended finding this little gem on VRBO. Would highly recommend, especially for families. Kids had a blast"
The price is NZ$840
includes taxes & fees
11 Jun - 12 Jun
Lakeside cottage overhanging the water, beautiful window views across the lake
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, (79)
"nice layout, plenty of room, great restaurant on the premises, we had a lovely stay and a great time."
Montauk Mansion With Outdoor Pool
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (54)
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (27)
"Rainy but good weekend"
The price is NZ$979
includes taxes & fees
13 Jun - 14 Jun
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
10.0 out of 10, Exceptional, (13)
"We just returned and loved our time at the villa! We chose to stay here for 2 nights of concerts at Mohegan sun and could not have been happier! The property is clean, comfortable and has everythign you could need. The snacks and water were a welcomed treat! Taylor was so accomodating and we hope to return one day!"
The price is NZ$526
includes taxes & fees
2 Jun - 3 Jun
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Cape Cod home in great location! Walk to downtown
9.4 out of 10, Exceptional, (120)
"Super cozy, homey, quiet and cute!"
Cape Cod home in great location! Walk to downtown
Charming Historic House in Downtown Mystic
10.0 out of 10, Exceptional, (111)
"We were in the area for a visit to local college, and we splurged on an overnight. So glad we did! Spotlessly clean, beautifully restored historical property right in the heart of a neighborhood and in walking distance to downtown. Comfortable beds, art supplies, games, and a well-appointed kitchen. Our daughter didn’t choose the college, but we will be back just to stay here again! Thank you for a truly special property."
The price is NZ$737
includes taxes & fees
16 Jun - 17 Jun
Charming Historic House in Downtown Mystic
Contemporary home, newly built, heated pool and hot tub, large deck and...
10.0 out of 10, Exceptional, (4)
"The property manager was incredibly helpful in providing check-in and check-out information, and was readily available to answer any questions during our stay. The house perfectly matched what we saw in the photos and was ideal for our getaway. We're already looking forward to returning in the summertime to fully enjoy the pool."
Contemporary home, newly built, heated pool and hot tub, large deck and...
Steps From The Beach! Watersports From Your Back Yard. 12 NEW SUP's & Kayaks
9.6 out of 10, Exceptional, (77)
"This property was spacious and well appointed. We had a large family gathering and this property gave us plenty of options for sleeping, eating, gathering and plenty of equipment for entertainment such as bikes, kayaks and paddle boards. I would definitely recommend this property! It was all we needed and much more. We hope to book again!"
Steps From The Beach! Watersports From Your Back Yard. 12 NEW SUP's & Kayaks
Lakeside cottage ON the water with beautiful views up the lake!
9.8 out of 10, Exceptional, (160)
"A traditional family lake cottage. Peaceful, quiet, and rented with love. Everything from the thoughtful little notes in the home to the paintings on the wall makes you feel cozy and welcomed. Everything you could need or want is provided. The hot tub under the stars, on the water is really the icing on the cake."
The price is NZ$883
includes taxes & fees
12 Jun - 13 Jun
Lakeside cottage ON the water with beautiful views up the lake!
Don't see what you're looking for?
See all available properties in Fishers Island
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.

Other types of properties in Fishers Island you may be interested in

Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino
3.5 star property
8.2 out of 10, Very good, (2097)
"It is quiet place for relax. room isclean."
The price is NZ$207
includes taxes & fees
20 Jun - 21 Jun
Bellissimo Hotel, Trademark by Wyndham Near Foxwoods Casino
Hilltop Inn & Suites - North Stonington
2.5 star property
8.2 out of 10, Very good, (1576)
"The room we stayed in seemed like it was newly renovated which was a bonus. Vety clean, spacious, convenient location (15 movies from downtown Mystic) and easy parking. The bed was very comfortable and the gentleman at the front desk was very nice. Perfect stay for our two day getaway to Mystic! "
The price is NZ$151
includes taxes & fees
11 Jun - 12 Jun
Hilltop Inn & Suites - North Stonington
Mohegan Sun
4.5 star property
9.2 out of 10, Wonderful, (1604)
"This place was amazing! I can literally live in there and never have to leave. It was an amazing stay, everything is very clean and there is something there for amy one and everyone. "
The price is NZ$434
includes taxes & fees
30 Jun - 1 Jul
Mohegan Sun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Fishers Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Fishers Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Fishers Island. Seeing all the best attractions is bound to make you fall in love with Fishers Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Fishers Island short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Fishers Island?

Yes, there are holiday rentals close to the most popular sights in Fishers Island, or you can select a more secluded option if you're looking for a relaxing stay. Fishers Island is known for its shopping and restaurants.

What are some of the best holiday rentals that Fishers Island has to offer?

Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!: This holiday home rental outside of Fishers Island is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

What can I see and do in Fishers Island?

Explore the area and cultural attractions such as Foxwoods Resort Casino, or visit one of the family-friendly sights such as Ocean Beach Park. In the wider area, you’ll find South Beach and Mohegan Sun Casino.

What are holiday rentals like in Fishers Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Fishers Island. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip.

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