Holiday Rentals in Surfside

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Holiday Rentals in Surfside

Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

10.0 out of 10, Exceptional, (253)
"The Eliza is a wonderful place to stay in Nantucket. It’s just a perfect little home conveniently located. The bed is very soft but does collapse in the center. It didn’t really hinder my sleep thankfully. A higher quality bathroom tissue would have also been appreciated. Overall, I’d highly recommend this home."
The price is €554
includes taxes & fees
10 Dec - 11 Dec
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town

10.0 out of 10, Exceptional, (85)
"We absolutely LOVED staying here. Close enough to downtown to walk but far out enough to be very quiet and peaceful. The space itself is very open and spacious while still feeling cozy and comfortable. We will definitely be back!"
2 Bedrooms + Loft - sleeps 6 in beds but max 4 adults- 5 Blocks to Town

Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!

10.0 out of 10, Exceptional, (111)
"Quaint cottage, good location Perfect for 2 people "
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!

Private Modern Bedroom In a Central Location

9.6 out of 10, Exceptional, (14)
"Jonathan was a really nice host - even showed us the oddity of the property shape, which was interesting. Very clean and new, would stay again!"
Private Modern Bedroom In a Central Location

Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St

10.0 out of 10, Exceptional, (58)
"Had a wonderful time. Loved the open concept of the house. Lots of light. Has everything that we needed. "
The price is €744
includes taxes & fees
30 Nov - 1 Dec
Swedish Blue and Yellow house new 2021! Just over a block to harbor and Main St

LUXURIOUS Cottage with Breathtaking Harbor Views

10.0 out of 10, Exceptional, (138)
"Clean, comfy beds, and a fabulous location! Easy walk to town and other locations. "
LUXURIOUS Cottage with Breathtaking Harbor Views

WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH | bikes & beach gear incl!

9.8 out of 10, Exceptional, (54)
"This is as described by other reviews - a comfortable older home in an unbeatable location - with deer wandering through the yard every day of our stay! We love Madaket! Richard was great ! We will be returning!"
WALK THROUGH THE MOORS BY LONG POND TO DIONIS BEACH | bikes & beach gear incl!

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (105)
"Very comfortable home, in a perfect location to attend the wedding of a close friend. 6 adults in the, able to walk to all the events. Peter, the host very gracious, allowing us not only an early check in, but also a later check out. Thank you Peter, we had a wonderful weekend. "
Beautifully Renovated Main Street Cottage- Great Location

Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!

10.0 out of 10, Exceptional, (207)
"We've stayed multiple times at this property because it is amazing! Great location, super clean, and Theresa is great to communicate with. Will keep coming back as long as she will have us!"
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

10.0 out of 10, Exceptional, (134)
"The house is adorable, clean and an easy walk to town. Nice outdoor area for dining or just sitting around when the weather allows. Theresa was quick to call with answers to any questions I had. Looking forward to staying there next year on my trip."
The price is €537
includes taxes & fees
1 Dec - 2 Dec
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (143)
"Visiting a niece working on the island for the summer. Planned the trip with this purpose to see family. It was wonderful and met all our expectations. 🥰❤️"
Renovated Cottage off Main Street- Great Location

Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!

10.0 out of 10, Exceptional, (210)
"We had an amazing stay at Millie Cottage! The house was beautifully maintained, cozy, and had everything we needed for a perfect family getaway—including our dog, who loved the yard!. The location was ideal; close to beaches, restaurants, downtown and all the charm Nantucket has to offer. Theresa and the property addressed every detail to make our stay comfortable and enjoyable. We can’t wait to return!"
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!

Mid Island Townhouse

9.2 out of 10, Wonderful, (5)
"Excellent place for stay during wedding. Host very responsive to questions. Highly recommend. "
Mid Island Townhouse

Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!

8.2 out of 10, Very good, (22)
"This is our second year staying here (see my previous review from August 2023) and we loved it as much as we did last year: easy, relaxed, comfortable, great location. One thing I’d mention is that there are no smoke detectors or carbon monoxide detectors in the house (which they say in the listing, it wasn’t a surprise), so if that is something that is important to you, I would recommend bringing your own. Otherwise, we had a great second stay here and would definitely return! Thanks for...
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!

OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.

10.0 out of 10, Exceptional, (81)
"Beautiful, cozy guesthouse. Very clean, simple nautical theme with lots of light. Tom Nevers is about 6 miles from the city center of Nantucket, but delightfully quiet with a beautiful beach. Absolutely no light pollution, so the unspoiled starry skies at night were a sight to behold!"
OCEAN VIEWS! Immaculate Quintessential Nantucket Beach Cottage see virtual tour.

FREE 3rd Night!* (See description) Nantucket in Town 3 Bedroom 1 Bath Cute House

9.6 out of 10, Exceptional, (43)
"Great location. House had everything needed. Just wished it had two bathrooms would have been easier but our week was great!"
FREE 3rd Night!* (See description) Nantucket in Town 3 Bedroom 1 Bath Cute House

Exquisite Oceanfont Cottage at Madaket Beach!

10.0 out of 10, Exceptional, (12)
"Fantastic property well aportioned and great communication. Would highly recommend"
Exquisite Oceanfont Cottage at Madaket Beach!

Spacious Beach Cottage with Grill, Patio, Outdoor Shower & High-Speed WiFi

8.0 out of 10, Very good, (19)
"This is a classic, rustic house and we absolutely loved it! The location is great- on the bike path and near Madaket beach, the backyard private with a lovely patio area. House is cozy and nice. Would stay again!"
Spacious Beach Cottage with Grill, Patio, Outdoor Shower & High-Speed WiFi

Nantucket - edge of town

9.8 out of 10, Exceptional, (74)
"Close to Town. 25 minute walk to Town. Midway point to all the beaches. Very helpful and responsive host. "
Nantucket - edge of town

Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!

8.8 out of 10, Excellent, (72)
"We found this property to be appropriately comfortable and well- laid out overall for our stay with two babies and our dogs. It is not a very fancy location or property, but served our needs well to spend time on our favorite island. The residential neighborhood is fairly noisy. I did appreciate the host’s communication and understanding for two potential issues- one huge one being a date change and then change back due to ferry car reservations. We did find that the other half of the property...
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!
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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Other types of properties in Surfside you may be interested in

Nantucket Inn

3.5 star property
8.8 out of 10, Excellent, (409)
"Excellent stay no complaints. "
The price is €168
includes taxes & fees
2 Dec - 3 Dec
Nantucket Inn

Faraway Nantucket

3.5 star property
8.6 out of 10, Excellent, (317)
"Perfect location, very clean, and helpful staff. We’ve been coming to the island for 10 years…we will definitely stay here again."
The price is €193
includes taxes & fees
4 Dec - 5 Dec
Faraway Nantucket

Jared Coffin House

4.0 star property
9.2 out of 10, Wonderful, (709)
"The location is as good as can be, bring VERY close to everything downtown Nantuvket has to offer plus provides off street parking. Entry ambience is old timey. There is no elevator so be prepared to climb if your room is above the first floor. Our top floor room could not be completely darkened due to the curtain arrangement. The room was chilly at first however staff quickly provided an electric heater which did the job. "
The price is €233
includes taxes & fees
1 Dec - 2 Dec
Jared Coffin House
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.

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.

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

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches: This holiday home rental outside of Surfside is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

How many holiday rentals are there in Surfside?

With 24 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 Miacomet Golf Course and Nantucket Historical Association.

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.