Surfside Vacation Rentals

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Vacation Rentals in Surfside

Harborview Nantucket

4.0 star property
9.6 out of 10, Exceptional, (13)
"We had an excellent stay at harbor view cottages! The property is beautiful and close to everything. it is clear that the owners paid attention to all the little details when furnishing the cottage, which I always appreciate. I will definitely be returning! "
The price is CA $965
CA $1,078 total
includes taxes & fees
Oct 2 - Oct 3
Harborview Nantucket

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

10.0 out of 10, Exceptional, (163)
"Beautiful cottage , great location. Would love to stay again "
The price is CA $669
CA $1,206 total
includes taxes & fees
Oct 4 - Oct 5
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

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

8.8 out of 10, Excellent, (78)
"Had a great time during our weekend trip to Nantucket. Property was in a great area and close to bus stop to get into town easily. Host was very responsive and easy to get a hold of. Only downsides were that the bathroom floors would get soaked during a shower even with the shower curtain and the basement felt slightly humid/moist. No tv in main living area. Other than those minor things would definitely recommend this property as an affordable option to stay in Nantucket "
Duplex Sunny Condo in residential neighborhood, 5min walk to bike paths!!!

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

10.0 out of 10, Exceptional, (222)
"Absolutely loved staying here. Great location and Theresa was super responsive! The property was well stocked and had everything we needed for a peaceful couple weeks. Our dogs loved being so close to the beach! "
The price is CA $785
CA $1,397 total
includes taxes & fees
Oct 2 - Oct 3
Luxurious Harbor View "Millie" Cottage! Walk & bike to everything!

LUXURIOUS Cottage with Breathtaking Harbor Views

9.8 out of 10, Exceptional, (164)
"Wonderful space in a great location! We are hoping to return again soon!"
The price is CA $785
CA $1,397 total
includes taxes & fees
Sep 28 - Sep 29
LUXURIOUS Cottage with Breathtaking Harbor Views

Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything

9.8 out of 10, Exceptional, (151)
"Adorable cottage just a short walk to town and ferry! "
The price is CA $924
CA $1,574 total
includes taxes & fees
Oct 3 - Oct 4
Luxurious Harbor View “Elizabeth” Cottage! Walk & bike to everything

Private Modern Bedroom In a Central Location

9.4 out of 10, Exceptional, (26)
"He property was beautiful. Very private, clean and plenty of space. The hosts are also super friendly. The property is close to a stop on the Miacomet line of The Wave. It’s about 1.5 miles from the middle of town and 2.5 miles from Surfside."
Private Modern Bedroom In a Central Location

Love Sand, Madaket on the Beach , Lovely Seaside Home

10.0 out of 10, Exceptional, (52)
"We thoroughly enjoyed our two nights and are sad to leave. The property is iconically Nantucket. Its location - and the views- is spectacular. It is well equipped for a relaxing family or couples vacation. Hope we can make it back. "
The price is CA $976
CA $2,100 total
includes taxes & fees
Sep 29 - Sep 30
Love Sand, Madaket on the Beach , Lovely Seaside Home

Cozy 4 bedroom cottage in town, with parking

2.0 star property
9.8 out of 10, Exceptional, (12)
"Great stay, would stay again "
Cozy 4 bedroom cottage in town, with parking

Renovated Cottage off Main Street- Great Location

10.0 out of 10, Exceptional, (158)
"The cabin was perfect. It was on more of a busy road than we anticipated, but everything else was wonderful. We enjoyed ourselves so much!!"
Renovated Cottage off Main Street- Great Location

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

8.4 out of 10, Very good, (25)
"The property was perfect for our family. It’s in a great location. We rented bikes and enjoyed being able to walk and bike to the beach and market. Thanks for letting us stay!"
Rustic, sunny cottage w/ deck & W/D - walk to the beach & town!

A Literary Oasis In The Heart Of Nantucket Town

10.0 out of 10, Exceptional, (79)
"We loved our stay at this property. We appreciated how spacious the apartment was and all of the design elements were thoughtful and beautiful. The best part was the location - right in town. I would not hesitate to stay here again. "
A Literary Oasis In The Heart Of Nantucket Town

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

10.0 out of 10, Exceptional, (278)
"What a perfect vacation spot. The home was perfect for two and well-appointed. Close to town and dining. Wonderful treasures to find on a walk. Would certainly book for our next trip to Nantucket. "
The price is CA $1,227
CA $1,918 total
includes taxes & fees
Sep 23 - Sep 24
Luxurious Harbor View “Eliza” Cottage! Next To White Elephant!

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

10.0 out of 10, Exceptional, (222)
"Run, don’t walk, to book this property! The location is fabulous for walking to Main Street. It’s beautifully furnished and comfortable. We were talking about coming back after the first night. Highly recommend!"
Luxurious Harbor View “Cynthia” cottage. Walk & bike to everything!

Enjoy Autumn On Nantucket in our Cozy, 1-bedroom condo with WiFi

9.6 out of 10, Exceptional, (4)
The price is CA $579
CA $1,081 total
includes taxes & fees
Sep 8 - Sep 9
Enjoy Autumn On Nantucket in our Cozy, 1-bedroom condo with WiFi

L0W TIDE, with Private Pool, Low Tide

10.0 out of 10, Exceptional, (44)
"We enjoyed our stay at the Low Tide. It is as pictured, easy to find and check-in. Host is lovely, good communication. If visiting Nantucket again, we would look to stay here again. Highly recommend."
The price is CA $1,095
CA $2,246 total
includes taxes & fees
Sep 8 - Sep 9
L0W TIDE, with Private Pool, Low Tide

Beautifully Renovated Main Street Cottage- Great Location

10.0 out of 10, Exceptional, (118)
"We were thrilled to arrive at our property with everything as pictured but actually more charming in person. It is easily walkable to town and restaurants. Communication with the owner was easy and I can recommend it to anyone who wants to stay on Nantucket. "
Beautifully Renovated Main Street Cottage- Great Location

Adorable guest house with saltwater pool and spa with views close to beach

9.6 out of 10, Exceptional, (4)
"My husband, dog and I loved our stay at Alesia’s property! The location was great, Alesia was very responsive and professional, and the space was clean and welcoming. We had a lovely time and highly recommend this spot to anyone looking for somewhere to stay on Nantucket. "
Adorable guest house with saltwater pool and spa with views close to beach

Stunning In-Town Home With Stone Hot Tub - Plunge Pool

10.0 out of 10, Exceptional, (26)
"We had three families staying with three kids aging 2-7 and one infant and it was the perfect amount of space! It was walking distance to all the shops and local restaurants. It was so clean! The owner was very helpful and responsive and friendly. "
The price is CA $3,851
CA $5,614 total
includes taxes & fees
Sep 29 - Sep 30
Stunning In-Town Home With Stone Hot Tub - Plunge Pool

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

10.0 out of 10, Exceptional, (118)
"Very cute place a short walk to town. House came equipped with everything we needed. "
The price is CA $675
CA $1,213 total
includes taxes & fees
Oct 3 - Oct 4
Luxurious Harbor View "Lizzie" Cottage! Walk & bike to everything!
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 Surfside Hotel Reviews

Find out more about Surfside

Find out more about Surfside

Everything you need to know about Surfside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Surfside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Surfside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Surfside vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Surfside. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Surfside vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Surfside vacation rentals we have selected for you start as low as CA $579 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Surfside rentals

At Expedia, we put the best Surfside vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Surfside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Surfside vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Surfside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a vacation rental in Surfside?

Yes, we offer vacation rentals close to well known local attractions in Surfside, or you can select a more remote option if you'd like a relaxing place to stay.

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

Cozy 4 bedroom cottage in town, with parking : You might want to consider this vacation rental near Surfside, which is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

How many vacation rentals are there in Surfside?

With 24 Expedia vacation rentals, you're sure 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 larger area, you’ll find Miacomet Golf Course and Nantucket Historical Association.

What’s a vacation rental in Surfside like?

Vacation rentals are private properties you can stay in for several days or longer in Surfside. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.