Vacation Rentals in Academy Hill, CT: Compare 10+ Sites & Save

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197 Best Vacation Rentals in Academy Hill (Starting from $81)

Florence
Florence
House
Milford, CT, USA
3.1k from Academy Hill center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

5 Bedrooms10 Guests
New to Booking
$340
Average price / night
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Landing | Stylish 1BD in South End Stratford
Landing | Stylish 1BD in South End Stratford
Apartment
Stratford, CT, 06615, United States
0.4k from Academy Hill center

AC, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$166
Average price / night
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coastal and cozy beach stay, pet friendly
coastal and cozy beach stay, pet friendly
House
Milford, CT, USA
3.2k from Academy Hill center

Security/Safety, Sports/Activities, Air Conditioner, Internet, Fireplace/Heating, Pet Friendly, View

3 Bedrooms5 Guests
New to Booking
$230
Average price / night
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Landing | Stunning Studio in South End Stratford
Landing | Stunning Studio in South End Stratford
Apartment
Stratford, CT, 06615, United States
0.4k from Academy Hill center

AC, Heater, Internet, Kitchen, No Smoking, TV, Washer

1 Bedroom2 Guests
New to Booking
$113
Average price / night
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Pet Friendly Milford Beachfront Home
Pet Friendly Milford Beachfront Home
House
Stratford, CT, USA
3.3k from Academy Hill center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

5 Bedrooms12 Guests
New to Booking
$1100
Average price / night
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Soothing Carriage House with Hot Tub in charming Stratford
Soothing Carriage House with Hot Tub in charming Stratford
House
Stratford, CT, 06615, United States
1.6k from Academy Hill center

AC, Fireplace, Free Parking, Heater, Hot Tub, Internet, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

11 reviews

$271
Average price / night
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Milford Entire House near Walnut Beach
Milford Entire House near Walnut Beach
Apartment
Milford, CT, USA
3.3k from Academy Hill center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Beach, Places to stay

2 Bedrooms4 Guests
9.5

Superb

2 reviews

$194
Average price / night
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Business or Weekend escape
Business or Weekend escape
House
Stratford, CT, 06615, United States
1.9k from Academy Hill center

AC, Barbecue, Extra Bed, Free Parking, Heater, Internet, Microwave, No Smoking, Outdoor Space

1 Bedroom4 Guests
9.2

Superb

53 reviews

$146
Average price / night
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Bobby's Beach Bungalow
Bobby's Beach Bungalow
House
Milford, CT, USA
3.5k from Academy Hill center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

3 Bedrooms6 Guests
8.0

Good

1 reviews

$270
Average price / night
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The ARLO - Walk to Brewery and Restaurants
The ARLO - Walk to Brewery and Restaurants
House
Milford, CT, 06460, United States
2.5k from Academy Hill center

AC, Arcade, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, No Smoking

2 Bedrooms5 Guests
9.6

Exceptional

5 reviews

$402
Average price / night
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The Lordship Loft
The Lordship Loft
House
Stratford, CT, USA
3.9k from Academy Hill center

B&bs, Accommodations, Parking, Guest houses, Homestays, Pet-friendly, Lodgings, Places to stay

1 Bedroom3 Guests
New to Booking
$170
Average price / night
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Cozy studio with 1 bedroom in peaceful Stratford retreat
Cozy studio with 1 bedroom in peaceful Stratford retreat
Apartment
Stratford, CT, 06614, United States
2.6k from Academy Hill center

AC, Dryer, Fitness Equipment, Heater, Internet, Laundry, No Smoking, Washer

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$81
Average price / night
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Akasa
Akasa
House
Stratford, CT, USA
4.1k from Academy Hill center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom10 Guests
New to Booking
$795
Average price / night
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3-bedroom building in cool Bridgeport neighborhood one block from Stratford CT.
3-bedroom building in cool Bridgeport neighborhood one block from Stratford CT.
House
Bridgeport, CT, 06610, United States
2.7k from Academy Hill center

AC, Heater, No Smoking

3 Bedrooms6 Guests
New to Booking
$333
Average price / night
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A little place in the Sun
A little place in the Sun
Apartment
Milford, CT, USA
5.2k from Academy Hill center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Beach, Jacuzzis

2 Bedrooms6 Guests
9.5

Superb

6 reviews

$703
Average price / night
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Beautiful 3-bedroom house in welcoming Stratford with AC
Beautiful 3-bedroom house in welcoming Stratford with AC
House
Stratford, CT, 06614, United States
2.7k from Academy Hill center

AC, Dryer, Heater, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$319
Average price / night
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Milford Vacation Rental about 1 Block to Beach!
Milford Vacation Rental about 1 Block to Beach!
Apartment
CT, USA
5.6k from Academy Hill center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$517
Average price / night
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FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!
FANTASTIC BEACHFRONT HOUSE- BEAUTIFUL VIEW AND BEACH, COME ENJOY !!!!
House
Milford, CT, 06460, United States
2.7k from Academy Hill center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.6

Exceptional

19 reviews

$1006
Average price / night
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Beachfront Connecticut Retreat with Views!
Beachfront Connecticut Retreat with Views!
House
Milford, CT, USA
6.0k from Academy Hill center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Beach

3 Bedrooms7 Guests
New to Booking
$276
Average price / night
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BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
BREATHTAKING BUNGALOW-HOME AWAY FROM HOME
House
Milford, CT, 06460, United States
2.7k from Academy Hill center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
10.0

Exceptional

44 reviews

$276
Average price / night
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1 minute walk to the beach - Private Beach Home
1 minute walk to the beach - Private Beach Home
House
Milford, CT, 06460, United States
2.7k from Academy Hill center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$373
Average price / night
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Fully Updated Home Near Wildemere Beach, Walk to Water, Pet Friendly Fenced Yard
Fully Updated Home Near Wildemere Beach, Walk to Water, Pet Friendly Fenced Yard
House
Milford, CT, 06460, United States
2.8k from Academy Hill center

AC, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

16 reviews

$711
Average price / night
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Charming 3-bedroom House In  Paradise Green Stratford CT Close To 95 & Train
Charming 3-bedroom House In Paradise Green Stratford CT Close To 95 & Train
House
Stratford, CT, 06614, United States
2.8k from Academy Hill center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$431
Average price / night
Check Availability
Classic cape, private beach, summer 2026, one month avail. July 8-Aug. 12
Classic cape, private beach, summer 2026, one month avail. July 8-Aug. 12
House
Milford, CT, 06460, United States
2.8k from Academy Hill center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$690
Average price / night
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Best Beach House in Milford—Sleeps 12 or so
Best Beach House in Milford—Sleeps 12 or so
House
Milford, CT, 06460, United States
3.0k from Academy Hill center

AC, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, No Smoking, Patio

4 Bedrooms12 Guests
New to Booking
$872
Average price / night
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Cozy 2 bedroom near Bridgeport Hospital
Cozy 2 bedroom near Bridgeport Hospital
Apartment
Bridgeport, CT, 06610, United States
3.0k from Academy Hill center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$110
Average price / night
Check Availability
Amazing 3BR Wildermere Beach Retreat, with Jacuzzi
Amazing 3BR Wildermere Beach Retreat, with Jacuzzi
House
Milford, CT, 06460, United States
3.0k from Academy Hill center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$407
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Academy Hill.

Where to stay in Academy Hill? Best neighborhoods & areas

Academy Hill Vacation Rentals on the Map

Frequently Asked Questions

You can explore 197 verified vacation rentals in Academy Hill. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Academy Hill vary depending on the season, property size, and location. Rates typically start from around $81 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Academy Hill include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Academy Hill welcome pets. Currently, 46 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Academy Hill often include amenities such as Fireplace/Heating, Laundry, and View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.