Vacation Rentals in Villages of Five Points, DE: Compare 10+ Sites & Save

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  6.  Villages of Five Points

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2110 Best Vacation Rentals in Villages of Five Points (Starting from $177)

Village of Five Points - 33322 E Chesapeake St UNIT 46
Village of Five Points - 33322 E Chesapeake St UNIT 46
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Accommodations, Pools, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$533
Average price / night
Check Availability
The Villages of Five Points apartment w/community pools, tennis courts, shops
The Villages of Five Points apartment w/community pools, tennis courts, shops
Apartment
Lewes, DE, 19958, United States
0.1k from Villages of Five Points center

AC, Balcony, Dryer, Free Parking, Heater, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$177
Average price / night
Check Availability
Village of Five Points - 17046 N Brandt St
Village of Five Points - 17046 N Brandt St
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Accommodations, Pools, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$265
Average price / night
Check Availability
Dog-friendly Villages of Five Points townhouse with pool, tennis, gym, grill
Dog-friendly Villages of Five Points townhouse with pool, tennis, gym, grill
House
Lewes, DE, 19958, United States
0.2k from Villages of Five Points center

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

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$367
Average price / night
Check Availability
Village of Five Points - 17059 S Brandt St Unit 3108
Village of Five Points - 17059 S Brandt St Unit 3108
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay

2 Bedrooms4 Guests
8.0

Good

2 reviews

$541
Average price / night
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FIVE POINTS OASIS - 3BR, 2.5BA - Sleeps 8 - Community Pool - Short Drive to Beach
FIVE POINTS OASIS - 3BR, 2.5BA - Sleeps 8 - Community Pool - Short Drive to Beach
House
Lewes, DE, 19958, United States
0.2k from Villages of Five Points center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$388
Average price / night
Check Availability
The Villages of Five Points - 17059 S Brandt St. Unit 3306
The Villages of Five Points - 17059 S Brandt St. Unit 3306
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$221
Average price / night
Check Availability
Village of Five Points townhouse with community pool, gym, and tennis access
Village of Five Points townhouse with community pool, gym, and tennis access
House
Lewes, DE, 19958, United States
0.2k from Villages of Five Points center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
8.6

Fabulous

4 reviews

$261
Average price / night
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4 Mi to Beaches Luxe Coastal Resort Condo
4 Mi to Beaches Luxe Coastal Resort Condo
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Condos

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$312
Average price / night
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Villages of Five Points Townhouse, Now Renting for 2026!
Villages of Five Points Townhouse, Now Renting for 2026!
House
Lewes, DE, 19958, United States
0.2k from Villages of Five Points center

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

3 Bedrooms8 Guests
10.0

Exceptional

55 reviews

$187
Average price / night
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Porch and Community Perks Walkable Lewes Condo
Porch and Community Perks Walkable Lewes Condo
Apartment
Lewes, DE, USA
0.1k from Villages of Five Points center

Apartments, Cheap, Accommodations, Pools, Parking, Spa, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
6.5

Good

2 reviews

$393
Average price / night
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Angela's Eclectic Villa: 3BR, 2.5BA - Sleeps 7 - Community Pool - Minutes from the Beach
Angela's Eclectic Villa: 3BR, 2.5BA - Sleeps 7 - Community Pool - Minutes from the Beach
House
Lewes, DE, 19958, United States
0.2k from Villages of Five Points center

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

3 Bedrooms7 Guests
9.8

Exceptional

29 reviews

$302
Average price / night
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Villages of Five Points - 17279 N Village Main Blvd.
Villages of Five Points - 17279 N Village Main Blvd.
House
Lewes, DE, USA
0.2k from Villages of Five Points center

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

3 Bedrooms7 Guests
New to Booking
$437
Average price / night
Check Availability
Townhome in Village of 5 Points, 3BDR 2.5BA Sleeps 6-8. Saturday-Saturday
Townhome in Village of 5 Points, 3BDR 2.5BA Sleeps 6-8. Saturday-Saturday
House
Lewes, DE, 19958, United States
0.3k from Villages of Five Points center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$362
Average price / night
Check Availability
4 Mi to Beaches Pet-Friendly Lewes Condo!
4 Mi to Beaches Pet-Friendly Lewes Condo!
Apartment
Lewes, DE, USA
0.2k from Villages of Five Points center

Apartments, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms5 Guests
9.7

Exceptional

4 reviews

$189
Average price / night
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Villages of Five Points Townhouse...Community Pools, Pickleball Courts & More!
Villages of Five Points Townhouse...Community Pools, Pickleball Courts & More!
House
Lewes, DE, 19958, United States
0.3k from Villages of Five Points center

AC, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$218
Average price / night
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The Villages of Five Points - 17405 N Village Main Blvd
The Villages of Five Points - 17405 N Village Main Blvd
House
Lewes, DE, USA
0.2k from Villages of Five Points center

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

3 Bedrooms8 Guests
New to Booking
$404
Average price / night
Check Availability
GOOD VIBES VILLA – 4BR, 2.5BA – Sleeps 12 – Community Pool – *Dog Friendly*
GOOD VIBES VILLA – 4BR, 2.5BA – Sleeps 12 – Community Pool – *Dog Friendly*
House
Lewes, DE, 19958, United States
0.3k from Villages of Five Points center

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

4 Bedrooms12 Guests
9.6

Exceptional

37 reviews

$394
Average price / night
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The Villages of Five Points - 17228 Chatham St
The Villages of Five Points - 17228 Chatham St
Apartment
Lewes, DE, USA
0.3k from Villages of Five Points center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$403
Average price / night
Check Availability
SUNDRENCHED REFLECTIONS – 4BD, 3.5BA – Sleeps 10 – Walkable community – Community Pool
SUNDRENCHED REFLECTIONS – 4BD, 3.5BA – Sleeps 10 – Walkable community – Community Pool
House
Lewes, DE, 19958, United States
0.3k from Villages of Five Points center

AC, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$280
Average price / night
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Crow's Nest - Private Guest Apt Near Bike Trail/3.7 mi to Beach
Crow's Nest - Private Guest Apt Near Bike Trail/3.7 mi to Beach
Apartment
Lewes, DE, USA
0.8k from Villages of Five Points center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$297
Average price / night
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SUNSET POINT VILLA – 4BR, 2.5BA – Sleeps 8 – Community Pool - Short drive to Beach
SUNSET POINT VILLA – 4BR, 2.5BA – Sleeps 8 – Community Pool - Short drive to Beach
House
Lewes, DE, 19958, United States
0.3k from Villages of Five Points center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
9.6

Exceptional

21 reviews

$394
Average price / night
Check Availability
Villages at Five Points Serenity | Beach
Villages at Five Points Serenity | Beach
House
Lewes, DE, 19958, United States
0.4k from Villages of Five Points center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
9.4

Superb

3 reviews

$269
Average price / night
Check Availability
Pet Friendly, Sleeps 10, 2 Community Pools, 4 Bikes, and Free Amenities, 10 Mins to the Beach
Pet Friendly, Sleeps 10, 2 Community Pools, 4 Bikes, and Free Amenities, 10 Mins to the Beach
House
Lewes, DE, 19958, United States
0.4k from Villages of Five Points center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$645
Average price / night
Check Availability
Pool/Tennis/Walking Paths! 33159 W Chesapeake Street
Pool/Tennis/Walking Paths! 33159 W Chesapeake Street
House
Lewes, DE, 19958, United States
0.4k from Villages of Five Points center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$369
Average price / night
Check Availability
**NEW 2026** 33151 W Chesapeake St.
**NEW 2026** 33151 W Chesapeake St.
House
Lewes, DE, 19958, United States
0.4k from Villages of Five Points center

AC, Barbecue, Dryer, Fireplace, Heater, Internet, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$468
Average price / night
Check Availability
Coastal Beauty-Bike to Beach
Coastal Beauty-Bike to Beach
House
Lewes, DE, 19958, United States
0.5k from Villages of Five Points center

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

3 Bedrooms8 Guests
New to Booking
$390
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 Villages of Five Points.

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Frequently Asked Questions

You can explore 2110 verified vacation rentals in Villages of Five Points. 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 Villages of Five Points vary depending on the season, property size, and location. Rates typically start from around $177 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 Villages of Five Points 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 Villages of Five Points welcome pets. Currently, 39 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 Villages of Five Points often include amenities such as Fireplace/Heating, Laundry, and Sports/Activities. 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.