House holiday rentals in Bridgeport
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Top-rated house rentals in Bridgeport
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Bridgeport house rentals
House rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
15–22 Apr
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
17–24 Oct
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
3–10 Feb
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
18–25 Sep
Home in Manorville
4.98 out of 5 average rating, 199 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
3–10 Oct
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
8–15 Oct
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
9–16 Jan
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
23–30 Sep
Weekly house rentals
Home in Milford
4.98 out of 5 average rating, 64 reviews2 Bedroom with sweeping views of Long Island Sound
8–15 May
Home in Bridgeport
4.98 out of 5 average rating, 65 reviewsCape on the Water
28 Oct – 4 Nov
Home in Fairfield
4.91 out of 5 average rating, 70 reviewsFairfield 2nd FL Suite w Private Entry & Parking
2–9 Jul
Home in Stratford
4.83 out of 5 average rating, 12 reviewsThe Rose
15–22 Apr
Home in Bridgeport
4.97 out of 5 average rating, 29 reviewsCatch some Zzz at Black Rock Harbor
7–14 Feb
Home in Fairfield
5.0 out of 5 average rating, 63 reviewsFairfield Cottage: Cozy retreat near Universities
9–16 Apr
Home in Bridgeport
5.0 out of 5 average rating, 38 reviewsKing Bed | 5 mins to SHU | Family Friendly |Grill
25 Aug – 1 Sep
Home in Fairfield
5.0 out of 5 average rating, 76 reviewsPeaceful Suburban Colonial w/New Kitchen.
11–18 Dec
Private house rentals
Home in Milford
4.9 out of 5 average rating, 20 reviewsQuiet and Cozy Getaway in Milford
3–10 Oct
Home in Bridgeport
4.88 out of 5 average rating, 8 reviews3BR 1st Floor Separate Entrance
6–13 Jun
Home in Milford
5.0 out of 5 average rating, 43 reviewsWalk to beach & shops. Luxe, designer renovation.
21–28 Oct
Home in Fairfield
5.0 out of 5 average rating, 8 reviewsStillson House - Central Cozy Updated Colonial
11–18 Jun
Home in Stratford
5.0 out of 5 average rating, 10 reviewsLordship Beach House - Pool & Beach (seasonal)
4–11 Nov
Home in Fairfield
5.0 out of 5 average rating, 15 reviews5 Minute Walk to Beach & Downtown Fairfield
5–12 Jan
Home in Milford
5.0 out of 5 average rating, 19 reviews“Little Blue” is all new!
24–31 Dec
Home in Trumbull
4.96 out of 5 average rating, 27 reviewsBeautiful Trumbull Home -Game Room, Backyard Oasis
3–10 Jul
Quick stats about house rentals in Bridgeport
Total rentals
130 properties
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
2.4K reviews
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