
Holiday rentals near Boomers! Medford
We found 1,025 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals within easy reach of Boomers! Medford that provide the perfect home base for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Boomers! Medford
Showing deals for:3 Oct - 10 Oct
Image gallery for Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

1010 out of 10 rating
Exceptional
(11 reviews)
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Riverhead, NY
8% off
Price is AU$7,949
AU$7,949
AU$1,136 per night
includes taxes & fees
Image gallery for A Beach Retreat In Ocean Bay Park, 4 Bedroom With Hot Tub

1010 out of 10 rating
Exceptional
(11 reviews)
A Beach Retreat In Ocean Bay Park, 4 Bedroom With Hot Tub
Ocean Bay Park, NY
8% off
Price is AU$12,955
AU$12,955
AU$1,851 per night
includes taxes & fees
Image gallery for NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Office space & Gym

1010 out of 10 rating
Exceptional
(10 reviews)
NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Office space & Gym
Westhampton, NY
6% off
Price is AU$9,552
AU$9,552
AU$1,365 per night
includes taxes & fees
Image gallery for Newly Renovated Luxury Beach House Ocean Bay Park

1010 out of 10 rating
Exceptional
(64 reviews)
Newly Renovated Luxury Beach House Ocean Bay Park
Bay Shore, NY
8% off
Price is AU$8,439
AU$8,439
AU$1,206 per night
includes taxes & fees
Image gallery for Brand new Interior and Exterior Family Beach House in Ocean Beach Fire Island NY

9.49.4 out of 10 rating
Exceptional
(9 reviews)
Brand new Interior and Exterior Family Beach House in Ocean Beach Fire Island NY
Ocean Beach, NY
8% off
Price is AU$13,541
AU$13,541
AU$1,934 per night
includes taxes & fees
Image gallery for Westhampton Beach Town and Country

9.89.8 out of 10 rating
Exceptional
(35 reviews)
Westhampton Beach Town and Country
Westhampton Beach, NY
8% off
Price is AU$12,222
AU$12,222
AU$1,746 per night
includes taxes & fees
Image gallery for Westhampton quintessential waterfront 2 acres w/ tennis, dock.

1010 out of 10 rating
Exceptional
(11 reviews)
Westhampton quintessential waterfront 2 acres w/ tennis, dock.
Westhampton Beach, NY
9% off
Price is AU$10,695
AU$10,695
AU$1,528 per night
includes taxes & fees
Image gallery for Hampton Retreat near the Beach

1010 out of 10 rating
Exceptional
(5 reviews)
Hampton Retreat near the Beach
Remsenburg, NY
16% off
Price is AU$5,286
AU$5,286
AU$755 per night
includes taxes & fees
Image gallery for #1 Rated Deluxe Hampton Estate: PICKLEBALL, Tennis, H Pool, 7 BDRM Videos!

9.49.4 out of 10 rating
Exceptional
(51 reviews)
#1 Rated Deluxe Hampton Estate: PICKLEBALL, Tennis, H Pool, 7 BDRM Videos!
Westhampton, NY
8% off
Price is AU$22,218
AU$22,218
AU$3,174 per night
includes taxes & fees
Image gallery for Private Home with Pool and Best Views in Ocean Beach! Docking for Private Boat.

1010 out of 10 rating
Exceptional
(5 reviews)
Private Home with Pool and Best Views in Ocean Beach! Docking for Private Boat.
Ocean Beach, NY
8% off
Price is AU$23,388
AU$23,388
AU$3,341 per night
includes taxes & fees
Image gallery for Chill Beachfront Cottage Amazing Bay & Sunset Views! Large Private Outdoor space

9.89.8 out of 10 rating
Exceptional
(37 reviews)
Chill Beachfront Cottage Amazing Bay & Sunset Views! Large Private Outdoor space
Bay Shore, NY
8% off
Price is AU$7,781
AU$7,781
AU$1,112 per night
includes taxes & fees
Image gallery for Large House for Big, Three-Generation Famiily! Labor Day Week Still Available!

1010 out of 10 rating
Exceptional
(10 reviews)
Large House for Big, Three-Generation Famiily! Labor Day Week Still Available!
Quogue, NY
17% off
Price is AU$19,499
AU$19,499
AU$2,786 per night
includes taxes & fees
Image gallery for Luxe Westhampton Beach Home w/ Pool & Hot Tub

1010 out of 10 rating
Exceptional
(9 reviews)
Luxe Westhampton Beach Home w/ Pool & Hot Tub
Westhampton Beach, NY
5% off
Price is AU$9,784
AU$9,784
AU$1,398 per night
includes taxes & fees
Image gallery for 4 Bedroom Home Steps from the Ocean

9.69.6 out of 10 rating
Exceptional
(17 reviews)
4 Bedroom Home Steps from the Ocean
Bay Shore, NY
8% off
Price is AU$13,793
AU$13,793
AU$1,970 per night
includes taxes & fees
Image gallery for Fire Island-pines-historic House-heated Pool AND HOT TUB

8.88.8 out of 10 rating
Excellent
(6 reviews)
Fire Island-pines-historic House-heated Pool AND HOT TUB
Sayville, NY
8% off
Price is AU$13,347
AU$13,347
AU$1,907 per night
includes taxes & fees
Image gallery for Great family rental - Roof top deck- Close to beach and close to town!

9.89.8 out of 10 rating
Exceptional
(13 reviews)
Great family rental - Roof top deck- Close to beach and close to town!
Ocean Beach, NY
14% off
Price is AU$9,657
AU$9,657
AU$1,380 per night
includes taxes & fees
Image gallery for Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

9.69.6 out of 10 rating
Exceptional
(37 reviews)
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Calverton, NY
15% off
Price is AU$3,727
AU$3,727
AU$532 per night
includes taxes & fees
Image gallery for 5 Star reviews Spectacular Ocean view Huge Deck Steps to the Ocean quite street

1010 out of 10 rating
Exceptional
(25 reviews)
5 Star reviews Spectacular Ocean view Huge Deck Steps to the Ocean quite street
Bay Shore, NY
7% off
Price is AU$12,071
AU$12,071
AU$1,724 per night
includes taxes & fees
Image gallery for Stunning, light-filled beach house with hot tub & sauna, minutes from the beach!

9.89.8 out of 10 rating
Exceptional
(8 reviews)
Stunning, light-filled beach house with hot tub & sauna, minutes from the beach!
Ocean Beach, NY
8% off
Price is AU$14,748
AU$14,748
AU$2,107 per night
includes taxes & fees
Image gallery for 3 Yrs Young HOME & Heated Salt Water POOL - equally convenient to Ocean or Bay!

1010 out of 10 rating
Exceptional
(10 reviews)
3 Yrs Young HOME & Heated Salt Water POOL - equally convenient to Ocean or Bay!
Ocean Beach, NY
7% off
Price is AU$12,045
AU$12,045
AU$1,721 per night
includes taxes & fees
Image gallery for Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.

1010 out of 10 rating
Exceptional
(61 reviews)
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
Westhampton Beach, NY
8% off
Price is AU$13,513
AU$13,513
AU$1,930 per night
includes taxes & fees
Image gallery for NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room

9.89.8 out of 10 rating
Exceptional
(11 reviews)
NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room
Eastport, NY
8% off
Price is AU$16,665
AU$16,665
AU$2,381 per night
includes taxes & fees
Image gallery for Newly Renovated and Private Hamptons Home

1010 out of 10 rating
Exceptional
(26 reviews)
Newly Renovated and Private Hamptons Home
Westhampton Beach, NY
8% off
Price is AU$11,257
AU$11,257
AU$1,608 per night
includes taxes & fees
Image gallery for Mastic Beach Surf House

1010 out of 10 rating
Exceptional
(10 reviews)
Mastic Beach Surf House
Mastic Beach, NY
8% off
Price is AU$3,580
AU$3,580
AU$511 per night
includes taxes & fees
Find spaces that suit your style
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Villa
Chalet
Find the best place to stay - Boomers! Medford
Showing deals for: 3 Oct - 6 OctWalk to Beach 2BR Near Dining & Shopping
Sleeps 6 · 2 bedrooms
6.66.6 out of 10
13 reviews(13 reviews)
The current price is AU$1,106
AU$1,106
for 3 nights, 1 apartment
AU$369 per night
includes taxes & fees
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
The current price is AU$2,048
AU$2,048
for 3 nights, 1 cottage
AU$683 per night
includes taxes & fees
1856 Trading House close to water
Sleeps 6 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
The current price is AU$1,915
AU$1,915
for 3 nights, 1 apartment
AU$638 per night
includes taxes & fees
Cozy Country Cottage #3
Sleeps 3 · 1 bedroom · 2 bathrooms
1010 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
The current price is AU$1,076
AU$1,076
for 3 nights, 1 cottage
AU$359 per night
includes taxes & fees
North Fork Escape
Sleeps 8 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
The current price is AU$2,764
AU$2,764
for 3 nights, 1 home
AU$921 per night
includes taxes & fees
The Jahmtons Guest Room
Sleeps 2 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
27 reviews(27 reviews)
The current price is AU$732
AU$732
for 3 nights, 1 room
AU$244 per night
includes taxes & fees
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value