Boston holiday homes
We found 4,601 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Boston, MA (BOS-All Airports)
Showing deals for:3 Oct - 10 Oct
Image gallery for 3 Bedrooms, 2 Baths Ranch Style Living on Spacious Intown Andover Location
1010 out of 10 rating
Exceptional
(21 reviews)
3 Bedrooms, 2 Baths Ranch Style Living on Spacious Intown Andover Location
Andover, MA
8% off
Price is NZ$6,745
NZ$6,745
NZ$964 per night
includes taxes & fees
Image gallery for NEW 2BR Historic Marblehead Home+Minutes to Beach
1010 out of 10 rating
Exceptional
(7 reviews)
NEW 2BR Historic Marblehead Home+Minutes to Beach
Marblehead, MA
8% off
Price is NZ$13,217
NZ$13,217
NZ$1,888 per night
includes taxes & fees
Image gallery for Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
1010 out of 10 rating
Exceptional
(16 reviews)
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Rockport, MA
8% off
Price is NZ$5,379
NZ$5,379
NZ$768 per night
includes taxes & fees
Image gallery for Fenway 2 bed 2 bath condo
8.88.8 out of 10 rating
Excellent
(5 reviews)
Fenway 2 bed 2 bath condo
Boston, MA
8% off
Price is NZ$12,701
NZ$12,701
NZ$1,814 per night
includes taxes & fees
Image gallery for Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Gloucester, MA
8% off
Price is NZ$4,544
NZ$4,544
NZ$649 per night
includes taxes & fees
Image gallery for Just a 5 Minute Walk to Short or Long Sands Beaches
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Just a 5 Minute Walk to Short or Long Sands Beaches
York Beach, ME
16% off
Price is NZ$3,562
NZ$3,562
NZ$509 per night
includes taxes & fees
Image gallery for Long Beach Suites: Steps To Beach, Newly Built
1010 out of 10 rating
Exceptional
(5 reviews)
Long Beach Suites: Steps To Beach, Newly Built
Gloucester, Massachusetts
8% off
Price is NZ$4,071
NZ$4,071
NZ$582 per night
includes taxes & fees
Image gallery for Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
Rockport, MA
8% off
Price is NZ$5,118
NZ$5,118
NZ$731 per night
includes taxes & fees
Image gallery for 2 Bd/2 Bth with ·King bed ·2 floors · Private Parking · Downtown Rockport
9.89.8 out of 10 rating
Exceptional
(8 reviews)
2 Bd/2 Bth with ·King bed ·2 floors · Private Parking · Downtown Rockport
Rockport, MA
8% off
Price is NZ$4,871
NZ$4,871
NZ$696 per night
includes taxes & fees
Image gallery for 2 BR CONDO 2 MIN. WALK TO OCEAN/BEACH
8.88.8 out of 10 rating
Excellent
(5 reviews)
2 BR CONDO 2 MIN. WALK TO OCEAN/BEACH
Hampton, NH
8% off
Price is NZ$2,891
NZ$2,891
NZ$413 per night
includes taxes & fees
Image gallery for Spacious suite - close to everything + backyard 10 min to Portsmouth +Ogunquit
1010 out of 10 rating
Exceptional
(5 reviews)
Spacious suite - close to everything + backyard 10 min to Portsmouth +Ogunquit
York, ME
12% off
Price is NZ$3,636
NZ$3,636
NZ$519 per night
includes taxes & fees
Image gallery for Former Carriage House on Plum Island Massachusetts
9.89.8 out of 10 rating
Exceptional
(69 reviews)
Former Carriage House on Plum Island Massachusetts
Newburyport, MA
8% off
Price is NZ$4,766
NZ$4,766
NZ$681 per night
includes taxes & fees
Image gallery for Magnificent Waterfront Home with Pool
1010 out of 10 rating
Exceptional
(7 reviews)
Magnificent Waterfront Home with Pool
Newburyport, MA
8% off
Price is NZ$15,944
NZ$15,944
NZ$2,278 per night
includes taxes & fees
Image gallery for Charming Coastal Cottage, Steps to Ocean & Rockport Village!
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Charming Coastal Cottage, Steps to Ocean & Rockport Village!
Rockport, MA
8% off
Price is NZ$5,074
NZ$5,074
NZ$725 per night
includes taxes & fees
Image gallery for The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·
9.89.8 out of 10 rating
Exceptional
(20 reviews)
The Bookstore · 2 Private Parking Spots · 2 King Beds · Downtown Rockport·
Rockport, MA
8% off
Price is NZ$5,253
NZ$5,253
NZ$750 per night
includes taxes & fees
Image gallery for 4BR, 4Bath Dream Home Experience: sauna, hot tub, pool. Explore Boston in Style!
9.49.4 out of 10 rating
Exceptional
(22 reviews)
4BR, 4Bath Dream Home Experience: sauna, hot tub, pool. Explore Boston in Style!
Newton, MA
8% off
Price is NZ$9,372
NZ$9,372
NZ$1,339 per night
includes taxes & fees
Image gallery for Walk to Good Harbor and Long Beach -Vacation Home
8.88.8 out of 10 rating
Excellent
(8 reviews)
Walk to Good Harbor and Long Beach -Vacation Home
Gloucester, MA
8% off
Price is NZ$5,074
NZ$5,074
NZ$725 per night
includes taxes & fees
Image gallery for Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed
Manchester-by-the-Sea, MA
8% off
Price is NZ$8,569
NZ$8,569
NZ$1,224 per night
includes taxes & fees
Image gallery for Summer at Rye Beach! Just down the street from Rye Harbor
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Summer at Rye Beach! Just down the street from Rye Harbor
Rye, NH
8% off
Price is NZ$7,164
NZ$7,164
NZ$1,023 per night
includes taxes & fees
Image gallery for Back-Bay Upscale Central Penthouse W Roof-top
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Back-Bay Upscale Central Penthouse W Roof-top
Boston, Massachusetts
16% off
Price is NZ$9,848
NZ$9,848
NZ$1,407 per night
includes taxes & fees
Image gallery for Tidy 2-Bed w/ Parking!🚗Wine!🍷UNH👩🏻🎓
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Tidy 2-Bed w/ Parking!🚗Wine!🍷UNH👩🏻🎓
Newmarket, NH
8% off
Price is NZ$2,686
NZ$2,686
NZ$384 per night
includes taxes & fees
Image gallery for Great for large group mins from DowntownBostonFenway Convention Grill Free Prkg
8.48.4 out of 10 rating
Very good
(6 reviews)
Great for large group mins from DowntownBostonFenway Convention Grill Free Prkg
Boston, MA
8% off
Price is NZ$10,702
NZ$10,702
NZ$1,529 per night
includes taxes & fees
Image gallery for 14b-Charming, beautiful 3-bedroom apartment in Boston
9.89.8 out of 10 rating
Exceptional
(7 reviews)
14b-Charming, beautiful 3-bedroom apartment in Boston
Boston, MA
6% off
Price is NZ$6,184
NZ$6,184
NZ$883 per night
includes taxes & fees
Image gallery for Plum Island Waterfront with 360 water views and roof deck!
1010 out of 10 rating
Exceptional
(15 reviews)
Plum Island Waterfront with 360 water views and roof deck!
Newbury, MA
8% off
Price is NZ$9,959
NZ$9,959
NZ$1,423 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Boston
Showing deals for: 28 Sept - 1 Oct
Take An Amazing Vacation! Pet-Friendly Property, Near Liberty Ride Trolley Tour!
Sleeps 4 · 1 bedroom · 1 bathroom
7.67.6 out of 10
Goodgood
12 reviews(12 reviews)
The current price is NZ$667
NZ$667
for 3 nights, 1 room
NZ$222 per night
includes taxes & fees
Barefoot'n Resort Kissimmee Orlando
Sleeps 4 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
111 reviews(111 reviews)
The current price is NZ$574
NZ$574
for 3 nights, 1 room
NZ$191 per night
includes taxes & fees
Lovely 2 bedroom condo 5 mins from downtown
Sleeps 4 · 2 bedrooms · 3 bathrooms
5.05.0 out of 10
2 reviews(2 reviews)
The current price is NZ$3,413
NZ$3,413
for 3 nights, 1 home
NZ$1,138 per night
includes taxes & fees
Serene Hotel w/ Indoor Pool and ArtBar Dining Near Harvard
Sleeps 4 · 1 bedroom · 1 bathroom
The current price is NZ$3,134
NZ$3,134
for 3 nights, 1 home
NZ$1,045 per night
includes taxes & fees
Fun, Family Friendly Restored Fire House 2 Bedroom Apt
Sleeps 6 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
142 reviews(142 reviews)
The current price is NZ$1,787
NZ$1,787
for 3 nights, 1 apartment
NZ$596 per night
includes taxes & fees
Graceland - Steps to the Beach
Sleeps 15 · 5 bedrooms · 1+ bathroom
The current price is NZ$2,229
NZ$2,229
for 3 nights, 1 home
NZ$743 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