Holiday rentals near Boomers! Medford
We found 1,008 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:21 Nov - 28 Nov
Image gallery for Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
9.49.4 out of 10 rating
Exceptional
(20 reviews)
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Riverhead, NY
8% off
Price is NZ$9,617
NZ$9,617
NZ$1,374 per night
includes taxes & fees
Image gallery for Peconic River Boatel
1010 out of 10 rating
Exceptional
(18 reviews)
Peconic River Boatel
Riverhead, NY
8% off
Price is NZ$5,975
NZ$5,975
NZ$854 per night
includes taxes & fees
Image gallery for NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym
1010 out of 10 rating
Exceptional
(11 reviews)
NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym
Westhampton, NY
6% off
Price is NZ$12,130
NZ$12,130
NZ$1,733 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
(12 reviews)
A Beach Retreat In Ocean Bay Park, 4 Bedroom With Hot Tub
Ocean Bay Park, NY
8% off
Price is NZ$14,733
NZ$14,733
NZ$2,105 per night
includes taxes & fees
Image gallery for Coastal Retreat Waterfront, Deck, Awesome Views
1010 out of 10 rating
Exceptional
(18 reviews)
Coastal Retreat Waterfront, Deck, Awesome Views
Wading River, NY
7% off
Price is NZ$10,031
NZ$10,031
NZ$1,433 per night
includes taxes & fees
Image gallery for Village Beach House
1010 out of 10 rating
Exceptional
(25 reviews)
Village Beach House
Westhampton Beach, NY
7% off
Price is NZ$14,914
NZ$14,914
NZ$2,131 per night
includes taxes & fees
Image gallery for Totally restored charming Sunny Hamptons home with heated salt water pool.
1010 out of 10 rating
Exceptional
(32 reviews)
Totally restored charming Sunny Hamptons home with heated salt water pool.
Westhampton, NY
8% off
Price is NZ$8,459
NZ$8,459
NZ$1,208 per night
includes taxes & fees
Image gallery for Westhampton Beach Town and Country
9.89.8 out of 10 rating
Exceptional
(37 reviews)
Westhampton Beach Town and Country
Westhampton Beach, NY
8% off
Price is NZ$14,672
NZ$14,672
NZ$2,096 per night
includes taxes & fees
Image gallery for OCEANFRONT BEACH HOUSE W/ POOL & HOT TUB FACING THE OCEAN-SUMMER LAST MIN DEALS!
1010 out of 10 rating
Exceptional
(25 reviews)
OCEANFRONT BEACH HOUSE W/ POOL & HOT TUB FACING THE OCEAN-SUMMER LAST MIN DEALS!
Westhampton Beach, NY
8% off
Price is NZ$28,676
NZ$28,676
NZ$4,097 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$12,785
NZ$12,785
NZ$1,826 per night
includes taxes & fees
Image gallery for Luxury Home with Hot Tub in Ocean Beach, Fire Island
1010 out of 10 rating
Exceptional
(5 reviews)
Luxury Home with Hot Tub in Ocean Beach, Fire Island
Ocean Beach, NY
7% off
Price is NZ$8,936
NZ$8,936
NZ$1,277 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
15% off
Price is NZ$5,234
NZ$5,234
NZ$748 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$26,801
NZ$26,801
NZ$3,829 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 NZ$8,714
NZ$8,714
NZ$1,245 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
(52 reviews)
#1 Rated Deluxe Hampton Estate: PICKLEBALL, Tennis, H Pool, 7 BDRM Videos!
Westhampton, NY
8% off
Price is NZ$27,663
NZ$27,663
NZ$3,952 per night
includes taxes & fees
Image gallery for Welcome to Westhampton
1010 out of 10 rating
Exceptional
(7 reviews)
Welcome to Westhampton
Westhampton, NY
7% off
Price is NZ$19,262
NZ$19,262
NZ$2,752 per night
includes taxes & fees
Image gallery for 4 BR 3 Bath with beautiful bay views and private heated pool seasonal
1010 out of 10 rating
Exceptional
(66 reviews)
4 BR 3 Bath with beautiful bay views and private heated pool seasonal
East Moriches, NY
7% off
Price is NZ$13,706
NZ$13,706
NZ$1,958 per night
includes taxes & fees
Image gallery for Modern Hamptons Getaway with Private Yard
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Modern Hamptons Getaway with Private Yard
East Moriches, NY
8% off
Price is NZ$4,480
NZ$4,480
NZ$640 per night
includes taxes & fees
Image gallery for Fall Delight of Hamptons Come Enjoy !
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Fall Delight of Hamptons Come Enjoy !
Westhampton Beach, NY
8% off
Price is NZ$10,371
NZ$10,371
NZ$1,482 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
(16 reviews)
Great family rental - Roof top deck- Close to beach and close to town!
Ocean Beach, NY
14% off
Price is NZ$10,246
NZ$10,246
NZ$1,464 per night
includes taxes & fees
Image gallery for NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room
9.29.2 out of 10 rating
Wonderful
(14 reviews)
NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room
Eastport, NY
7% off
Price is NZ$25,355
NZ$25,355
NZ$3,622 per night
includes taxes & fees
Image gallery for Newly Renovated and Private Hamptons Home
1010 out of 10 rating
Exceptional
(27 reviews)
Newly Renovated and Private Hamptons Home
Westhampton Beach, NY
7% off
Price is NZ$13,464
NZ$13,464
NZ$1,923 per night
includes taxes & fees
Image gallery for Escape to this FIRE ISLAND PINES BEACH HOME with Heated Salt Water Pool
1010 out of 10 rating
Exceptional
(13 reviews)
Escape to this FIRE ISLAND PINES BEACH HOME with Heated Salt Water Pool
Sayville, NY
8% off
Price is NZ$26,287
NZ$26,287
NZ$3,755 per night
includes taxes & fees
Image gallery for Beautiful Beach House with Large Swimming Pool in Ocean Beach
1010 out of 10 rating
Exceptional
(35 reviews)
Beautiful Beach House with Large Swimming Pool in Ocean Beach
Ocean Beach, NY
7% off
Price is NZ$6,466
NZ$6,466
NZ$924 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
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Sleeps 24 · 11 bedrooms · 9+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Walk to Beach 2BR Near Dining & Shopping
Sleeps 6 · 2 bedrooms
6.66.6 out of 10
18 reviews(18 reviews)
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
40 reviews(40 reviews)
Meets Modern Comfort in This 3-Bedroom Long Island Sound Retreat
Sleeps 8 · 3 bedrooms · 3 bathrooms
6.86.8 out of 10
6 reviews(6 reviews)
Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
104 reviews(104 reviews)
The Jahmtons Guest Room
Sleeps 2 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
28 reviews(28 reviews)
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