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
7% off
Price is NZ$8,783
NZ$8,783
NZ$1,255 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
7% off
Price is NZ$14,377
NZ$14,377
NZ$2,054 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 NZ$10,253
NZ$10,253
NZ$1,465 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 NZ$9,076
NZ$9,076
NZ$1,297 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 NZ$15,306
NZ$15,306
NZ$2,187 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
8% off
Price is NZ$11,997
NZ$11,997
NZ$1,714 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 NZ$13,604
NZ$13,604
NZ$1,943 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 NZ$5,716
NZ$5,716
NZ$817 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 NZ$25,200
NZ$25,200
NZ$3,600 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 NZ$26,536
NZ$26,536
NZ$3,791 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
7% off
Price is NZ$8,597
NZ$8,597
NZ$1,228 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 NZ$22,100
NZ$22,100
NZ$3,157 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 NZ$10,498
NZ$10,498
NZ$1,500 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 NZ$15,593
NZ$15,593
NZ$2,228 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 NZ$15,085
NZ$15,085
NZ$2,155 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 NZ$10,362
NZ$10,362
NZ$1,480 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 NZ$4,048
NZ$4,048
NZ$578 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 NZ$16,683
NZ$16,683
NZ$2,383 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 NZ$13,416
NZ$13,416
NZ$1,917 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 NZ$15,276
NZ$15,276
NZ$2,182 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
7% off
Price is NZ$18,869
NZ$18,869
NZ$2,696 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 NZ$12,595
NZ$12,595
NZ$1,799 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 NZ$3,888
NZ$3,888
NZ$555 per night
includes taxes & fees
Image gallery for Get out of city. Luxury Family Retreat; Pool, Putting Green, great outdoor deck
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Get out of city. Luxury Family Retreat; Pool, Putting Green, great outdoor deck
Westhampton, NY
8% off
Price is NZ$16,444
NZ$16,444
NZ$2,349 per night
includes taxes & fees
Find spaces that suit your style
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Cabin
Cottage
Villa
Chalet
Find the best place to stay - Boomers! Medford
Showing deals for: 2 Oct - 5 Oct
Walk to Beach 2BR Near Dining & Shopping
Sleeps 6 · 2 bedrooms
6.66.6 out of 10
13 reviews(13 reviews)
The current price is NZ$1,183
NZ$1,183
for 3 nights, 1 apartment
NZ$394 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 NZ$2,222
NZ$2,222
for 3 nights, 1 cottage
NZ$741 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 NZ$2,217
NZ$2,217
for 3 nights, 1 apartment
NZ$739 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 NZ$1,169
NZ$1,169
for 3 nights, 1 cottage
NZ$390 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 NZ$3,002
NZ$3,002
for 3 nights, 1 home
NZ$1,001 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 NZ$850
NZ$850
for 3 nights, 1 room
NZ$283 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
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