Surfside Holiday Rentals

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Holiday Rentals in Surfside

Two-bedroom cottage with one Queen-size bed, two twin beds, and a sofa bed.
9.0 out of 10, Wonderful, (8)
"We enjoyed our stay!"
Two-bedroom cottage with one Queen-size bed, two twin beds, and a sofa bed.
2 Bedrooms plus Loft - sleeps 6 in beds - 5 Blocks to Center of Town
10.0 out of 10, Exceptional, (74)
"5 Honeysuckle Ln. is an absolutely perfect little cottage that is welcoming and has everything you need for your stay on Nantucket. It had all the comfort of home and I loved sleeping in the loft. It was like a little piece of heaven, looking out the window up there. Our dear friends, enjoyed the master bedroom which had a wonderful king bed, and so much room to sort themselves out during our vacation. We didn’t require the twin bedroom so we used it as a dressing room and that worked...
2 Bedrooms plus Loft - sleeps 6 in beds - 5 Blocks to Center of Town
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything
9.8 out of 10, Exceptional, (132)
"Cute and cozy for a small family."
The price is NZ$2,200
includes taxes & fees
6 Jun - 7 Jun
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything
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Quiet getaway for two
9.6 out of 10, Exceptional, (51)
"Perfect little spot!"
Quiet getaway for two
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
8.0 out of 10, Very good, (11)
"We loved this house. Sure, it is rustic (as the title says), but we loved the vibe. The architecture, exposed wood, and white floors felt like a 60s surf bungalow. The house is interesting and there are some quirks, but nothing that had any impact on our stay. It was clean and well appointed where it mattered- the linens were clean and fresh, the kitchen and bathroom were clean, the mattresses on the twin beds seemed new. It was walking distance to the little town, beach, playground, Sconset...
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!
Ireland Time | House in Nantucket with deck, full kitchen, & W/D
8.0 out of 10, Very good, (1)
Ireland Time | House in Nantucket with deck, full kitchen, & W/D
Tranquilty
10.0 out of 10, Exceptional, (29)
"The hosts were very nice accommodating and welcoming. The property exceeding our expectations and would love to stay there again in the future."
Tranquilty
LUXURIOUS Cottage with Breathtaking Harbor Views
9.8 out of 10, Exceptional, (125)
"Theresa’s property is perfect for a small group trip. My family and I stayed for the week and couldn’t have been happier with the location, cleanliness, and comfort of the home. Truly felt like we were in our own little paradise! We will definitely be back."
The price is NZ$1,546
includes taxes & fees
5 Jun - 6 Jun
LUXURIOUS Cottage with Breathtaking Harbor Views
Nantucket - edge of town
9.8 out of 10, Exceptional, (67)
"Nice rental,Stayed only one night but will definitely be back"
The price is NZ$1,397
includes taxes & fees
11 Jun - 12 Jun
Nantucket - edge of town
Private Modern Bedroom In a Central Location
9.0 out of 10, Wonderful, (6)
"It was great"
The price is NZ$830
includes taxes & fees
2 Jul - 3 Jul
Private Modern Bedroom In a Central Location
Beautifully Renovated Main Street Cottage- Great Location
10.0 out of 10, Exceptional, (95)
"My family of four plus a dog were very comfortable in this cottage. The cottage is beautiful and well stocked. Beds were comfy. Kitchen is also well stocked. Location was great. We walked easily into town or rode bikes to various beaches. All in all this is a great rental property."
Beautifully Renovated Main Street Cottage- Great Location
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
10.0 out of 10, Exceptional, (113)
"We stayed here for a few days after our wedding and it was perfect. Private, walkable and clean."
The price is NZ$897
includes taxes & fees
5 Jun - 6 Jun
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
10.0 out of 10, Exceptional, (99)
"The location of this property is amazing. Right across from the water and walkable to downtown/the central bus terminal. The property itself was beautiful and nicely appointed."
The price is NZ$1,898
includes taxes & fees
6 Jun - 7 Jun
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
Renovated Cottage off Main Street- Great Location
10.0 out of 10, Exceptional, (138)
"This was our first time visiting Nantucket and we could not have had a better time! The cottage was great and the centralized location could not have been better."
Renovated Cottage off Main Street- Great Location
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
8.8 out of 10, Excellent, (61)
"Accommodations were as expected. Communication with the host was great."
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
Sail Away Cottage | Dog-friendly house in Nantucket with indoor/outdoor living
10.0 out of 10, Exceptional, (4)
"We loved visiting off season. It was a wonderful way to see the island."
Sail Away Cottage | Dog-friendly house in Nantucket with indoor/outdoor living
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
10.0 out of 10, Exceptional, (195)
"Millie’s was a great place for our family to stay. It is well decorated, clean, and very comfortable. The location is close to everything in town where our kids were able to walk with us to get coffee, shop, and relax. Thank you Theresa!"
The price is NZ$2,233
includes taxes & fees
9 Jun - 10 Jun
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!
2 Bedrooms Plus Loft - Sleeps 6 in Beds - 5 Blocks to Center of Town
10.0 out of 10, Exceptional, (89)
"We loved our stay at Honeysuckle Right. From the moment we walked in, we were in love with the decor, sleeping accommodations and distance to town. Exceeded our expectations! Look forward to a return stay."
2 Bedrooms Plus Loft - Sleeps 6 in Beds - 5 Blocks to Center of Town
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
10.0 out of 10, Exceptional, (235)
"Perfect for a couple."
The price is NZ$2,165
includes taxes & fees
19 Jun - 20 Jun
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!
Peaceful, Private Island Home On Tuckernuck, Nantucket
10.0 out of 10, Exceptional, (11)
"We met John, our gracious host, at the dock in Madaket. He took us to Tuckernuck by boat past and through the many natural wonders of the area. Our group had plans to surf cast every day and John made sure to point out some great spots as we approached. Once landed it was a short walk up to “The Decoy,” his family’s historic cottage. Getting on the island does involve getting your feet wet so bring some water shoes or sandals. Once there, John gave us a tour of the house and a brief history of...
Peaceful, Private Island Home On Tuckernuck, Nantucket
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See all available properties in Surfside
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 Surfside you may be interested in

Jared Coffin House
4.0 star property
9.0 out of 10, Wonderful, (563)
"Great hospitality!"
The price is NZ$668
includes taxes & fees
9 Jun - 10 Jun
Jared Coffin House
Faraway Nantucket
3.5 star property
8.8 out of 10, Excellent, (219)
"Amazing!! "
The price is NZ$498
includes taxes & fees
5 Jun - 6 Jun
Faraway Nantucket
Nantucket Inn
3.5 star property
8.4 out of 10, Very good, (286)
"Quick stay. Convenient check in. Very comfortable room. "
The price is NZ$924
includes taxes & fees
10 Jun - 11 Jun
Nantucket Inn
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 Surfside 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 Surfside. 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 Surfside. Seeing all the best attractions is bound to make you fall in love with Surfside. 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 Surfside short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Surfside?

Yes, there are holiday rentals close to the most popular sights in Surfside, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Surfside?

With 25 Expedia holiday rentals, you're guaranteed to find just the right place for your Surfside stay.

What’s there to see and do in Surfside?

Surfside Beach and Nobadeer Beach are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Nantucket Historical Association and Nantucket Atheneum.

What’s a holiday rental in Surfside like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Surfside. Holiday rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.

Recent reviews of Surfside properties
Expedia verified reviews