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Medford Holiday Rentals

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Our top choices for Medford holiday rentals

Cottage in Miller Place

Cozy Country Cottage #4
10.0 out of 10, Exceptional, (15)
"Lovely cottage with great host! All was wonderful!! very happy with our 17 day vacation!"
United States
Laurita S.
The price is NZ$564
includes taxes & fees
26 Dec - 27 Dec
Cozy Country Cottage #4

Apartment in Mastic

South Shore Studio in Mastic
2.0 star property
10.0 out of 10, Exceptional, (2)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is NZ$331
includes taxes & fees
6 Jan - 7 Jan 2026
South Shore Studio in Mastic
10.0 out of 10, Exceptional, (3)
"Would definitely stay again "
United States
Katherine R.
The price is NZ$345
includes taxes & fees
13 Jan - 14 Jan 2026
JC Entire Apartment remodeled, close to Airport and Ferry

Apartment in Central Islip

Cozy 2 bedroom retreat in long island
2.0 star property
8.8 out of 10, Excellent, (3)
"Apt was clean and comfortable. Beds were comfortable. Area was nice. Owner communication was good. Only drawback is the plumbing situation was not advertised in the listing. Iif you are comfortable using a bidet and not flushing paper, this apt is perfect. "
United States
Deborah R.
The price is NZ$430
includes taxes & fees
27 Dec - 28 Dec
Cozy 2 bedroom retreat in long island
7.8 out of 10, Good, (10)
"I answered this. Safe and Quit."
United States
John
The price is NZ$584
includes taxes & fees
28 Dec - 29 Dec
Spacious one Bedroom Apt with private entrance
10.0 out of 10, Exceptional, (16)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is NZ$309
includes taxes & fees
28 Dec - 29 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
8.4 out of 10, Very good, (6)
"We wanted an inexpensive place to stay out on Long Island for July 4th weekend. We were a 15-20 minute drive to the beautiful beaches of Robert Moses and a 2 hour drive from Montauk.We were able to stay for a very reasonable price over a notoriously expensive weekend.Jenelle's communication was direct, welcoming and helpful.We would definitely stay here again!"
United States
Melanie M.
The price is NZ$342
includes taxes & fees
26 Dec - 27 Dec
Tiny Home Private, Students, Nurses, Tech
2.0 star property
The price is NZ$649
includes taxes & fees
26 Dec - 27 Dec
Cozy and Modern 2-bedroom apartment in lovely Yaphank
10.0 out of 10, Exceptional, (22)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
The price is NZ$1,076
includes taxes & fees
30 Dec - 31 Dec
3 Story Beach Waterview, 3 KING bed, golf putting green!
9.4 out of 10, Exceptional, (6)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is NZ$463
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy king suite with kitchen and dining area.
9.6 out of 10, Exceptional, (26)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is NZ$454
includes taxes & fees
4 Jan - 5 Jan 2026
Private 1 bedroom apt in a quiet neighborhood, close to all!
The price is NZ$239
includes taxes & fees
1 Jan - 2 Jan 2026
Fabulous 1-bedroom, 1 bathroom Hotel inspired Room in Ronkonkoma
9.4 out of 10, Exceptional, (36)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
The price is NZ$284
includes taxes & fees
27 Dec - 28 Dec
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
10.0 out of 10, Exceptional, (1)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
The price is NZ$384
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful private 2-bedroom house in Bayport.Amazing location!
8.6 out of 10, Excellent, (8)
"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 NZ$1,147
includes taxes & fees
24 Dec - 25 Dec
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was beautiful inside and out. The host was very responsive. The furnishings where comfortable. Area was very nice with the pond. Although there was a canoe availabe we didnt use dew to our age.lol there where other amenities we didnt use either fire pit a barbecue grill and other outdoor zen spots. We highly recomend this host."
United States
Gregory D.
The price is NZ$449
includes taxes & fees
4 Jan - 5 Jan 2026
Lakefront GetawaY & Romantic NightS + BeacheS NeaR

Cottage in Miller Place

Cozy Country Cottage #3
10.0 out of 10, Exceptional, (32)
"Fantastic stay! "
United States
Michael V.
The price is NZ$556
includes taxes & fees
28 Dec - 29 Dec
Cozy Country Cottage #3
10.0 out of 10, Exceptional, (23)
"Pet friendly "
United States
Steven
The price is NZ$913
includes taxes & fees
1 Jan - 2 Jan 2026
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
10.0 out of 10, Exceptional, (4)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is NZ$1,064
includes taxes & fees
2 Jan - 3 Jan 2026
Modern Vacation home. Close to The Hamptons

Apartment in Bay Shore

1 bedroom 1 bath private entrance
8.8 out of 10, Excellent, (22)
"Well suited for our needs."
United States
Teresa D.
The price is NZ$339
includes taxes & fees
24 Dec - 25 Dec
1 bedroom 1 bath private entrance
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 Medford Hotel Reviews

Find out more about Medford

Everything you need to know about Medford holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Medford holiday rental for you. At Expedia, you can take your pick from private holiday 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 Medford holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Medford holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Medford. 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 Medford holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Medford holiday rentals we have selected for you start as low as NZ$284 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Medford rentals

At Expedia, we put the best Medford holiday 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 Medford 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 Medford holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Medford. 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 holiday rentals in Medford?

Yes, there are holiday rentals in Medford close to Boomers! Medford, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Medford. Make sure you have time to check out the baseball games and beaches during your trip.

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

4-bedroom beach house minutes from Hamptons: This holiday home rental outside of Medford offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

What can I see and do in Medford?

Family-friendly attractions include Boomers! Medford and Country Fair Entertainment Park, whereas Carmans River is a spot to enjoy the outdoors. Lasorda Legacy Park and 89 North Music Venue are a couple of places you'll find in the wider area.

What are holiday rentals like in Medford?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Medford. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the excitement and 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 choice for small groups.