Holiday rentals in Bridgeport

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Top-rated holiday rentals in Bridgeport

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest suite in Fairfield
Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen
Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.
5–12 Oct
$133 SGD per night
4.92 out of 5 average rating, 109 reviews
Guest favourite
Guest suite in Fairfield
Adorable private apt w/ W/D in lovely neighborhood
Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.
1–8 Nov
$120 SGD per night
4.92 out of 5 average rating, 106 reviews
Guest favourite
Flat in Milford
Water front studio apartment with fireplace.
This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!
28 Aug – 4 Sep
$234 SGD per night
4.97 out of 5 average rating, 505 reviews

Popular amenities for Bridgeport holiday rentals

Stay near Bridgeport's top sights

Seaside Park31 locals recommend
Connecticut's Beardsley Zoo63 locals recommend
Whole Foods Market33 locals recommend
Bass Pro Shops8 locals recommend
Bow Tie Cinemas Marquis 1613 locals recommend
Pantanal13 locals recommend

Other great holiday rentals in Bridgeport

Guest favourite
Guest suite in Shelton
Super cozy 1 BR apt. own entrance, great loc.
7–14 Aug
$69 SGD per night
4.81 out of 5 average rating, 260 reviews
Guest favourite
Home in Milford
The Daydreamer -Walk to Walnut Beach, Pet Friendly
26 Oct – 2 Nov
$268 SGD per night
4.99 out of 5 average rating, 220 reviews
Guest favourite
Flat in Bridgeport
Ricport Studio 6
19–26 May
$197 SGD per night
5.0 out of 5 average rating, 31 reviews
Superhost
Flat in Bridgeport
Lovely 1 bedroom cozy modern apartment w/75” 4K TV
15–22 Dec
$126 SGD per night
4.83 out of 5 average rating, 36 reviews
Guest favourite
Flat in Bridgeport
Polita’s Place # 2
3–10 May
$133 SGD per night
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Fairfield
Fairfield 2nd FL Suite w Private Entry & Parking
6–13 May
$120 SGD per night
4.91 out of 5 average rating, 65 reviews
Guest favourite
Flat in Milford
The Pond Mill Retreat w/ 2 Bdrms & Pool
30 Mar – 6 Apr
$165 SGD per night
5.0 out of 5 average rating, 46 reviews
Superhost
Home in Fairfield
Fairfield 2nd FL Suite w Private Entry & Parking
11–18 Jun
$127 SGD per night
4.9 out of 5 average rating, 30 reviews
Guest favourite
Flat in Bridgeport
Seaside Studio in Historic Bridgeport Brownstone
23–30 Jun
$125 SGD per night
4.89 out of 5 average rating, 64 reviews
Guest favourite
Flat in Bridgeport
Lovely 2bdrm in cozy neighborhood!
3–10 Jul
$195 SGD per night
4.94 out of 5 average rating, 32 reviews
Guest favourite
Cabin in Milford
Long Stays! Charming Coast Cabin| Near Beach| Pets
12–19 Apr
$111 SGD per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Guest house in Milford
The studio downtown
21–28 Jul
$153 SGD per night
5.0 out of 5 average rating, 30 reviews

Quick stats about holiday rentals in Bridgeport

Total rentals

270 properties

Rentals with dedicated workspaces

170 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

60 properties allow pets

Family-friendly rentals

120 properties are a good fit for families

Total number of reviews

5.2K reviews

Destinations to explore