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Chesapeake Holiday Apartments

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50 rentals in Chesapeake.
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Welcome to Our Cozy Home in Chesapeake, holiday rental in Chesapeake

Welcome to Our Cozy Home in Chesapeake

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Nestled out in the country -2, holiday rental in Chesapeake

Nestled out in the country -2

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business dist, holiday rental in Chesapeake

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business dist

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!, holiday rental in Chesapeake

Free Breakfast. Indoor Pool & Hot Tub. Your Next Trip!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Otter's Den, holiday rental in Chesapeake

Tentrr Signature Site - Otter's Den

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Quaint Southern House with pool & lake (Cleaned & Sanitized), holiday rental in Chesapeake

Quaint Southern House with pool & lake (Cleaned & Sanitized)

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Chic's Beach Living II, holiday rental in Chesapeake

Chic's Beach Living II

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Just 400 Ft To The Beach!!, holiday rental in Chesapeake

Just 400 Ft To The Beach!!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Fantastic, Spacious family vacation home, holiday rental in Chesapeake

Fantastic, Spacious family vacation home

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lovely Town Home Driving Distance to the Beach, holiday rental in Chesapeake

Lovely Town Home Driving Distance to the Beach

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Furnished Short term rental, holiday rental in Chesapeake

Furnished Short term rental

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfy King Bed/In the Heart of VB, holiday rental in Chesapeake

Comfy King Bed/In the Heart of VB

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Waterfront Cottage Near Downtown Norfolk with Private Dock and Sunroom, holiday rental in Chesapeake

Beautiful Waterfront Cottage Near Downtown Norfolk with Private Dock and Sunroom

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious Town home Located 20 Minutes from the Virginia Beach Ocean Front., holiday rental in Chesapeake

Spacious Town home Located 20 Minutes from the Virginia Beach Ocean Front.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach Cottage Coral Suite, holiday rental in Chesapeake

Beach Cottage Coral Suite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beachy townhouse on the golf course, holiday rental in Chesapeake

Beachy townhouse on the golf course

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Live history, dont just visit!, holiday rental in Chesapeake

Live history, dont just visit!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Your Home Away From Home, holiday rental in Chesapeake

Your Home Away From Home

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beach Cottage Wave Suite, holiday rental in Chesapeake

Beach Cottage Wave Suite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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GRANDMAs QUIET WATERFRONT HOME, holiday rental in Chesapeake

GRANDMAs QUIET WATERFRONT HOME

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach Decor Bungalow Centrally Located, holiday rental in Chesapeake

Beach Decor Bungalow Centrally Located

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Chic's Nest, holiday rental in Chesapeake

Chic's Nest

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome Military Welcome Civilians Welcome All, holiday rental in Chesapeake

Welcome Military Welcome Civilians Welcome All

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Minutes to Bay Beaches and Base! Spread out in this Spacious Mid-Century Ranch, holiday rental in Chesapeake

Minutes to Bay Beaches and Base! Spread out in this Spacious Mid-Century Ranch

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Love's Nest is a wonderful townhome in Virginia Beach., holiday rental in Chesapeake

Love's Nest is a wonderful townhome in Virginia Beach.

2 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Ship’s Inn; The Lighthouse Cottage (Beach View), holiday rental in Chesapeake

Ship’s Inn; The Lighthouse Cottage (Beach View)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Modern Barn at Hunt Club Farm, holiday rental in Chesapeake

The Modern Barn at Hunt Club Farm

6 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Mother-in-Law Suite, holiday rental in Chesapeake

Cozy Mother-in-Law Suite

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Stately Norfolk Home w/Yard + Grill: Walk to Beach, holiday rental in Chesapeake

Stately Norfolk Home w/Yard + Grill: Walk to Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach Side Studio #5 - Pet Friendly, holiday rental in Chesapeake

Beach Side Studio #5 - Pet Friendly

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Ships Inn: The Captain's Cabin (Beach View), holiday rental in Chesapeake

Ships Inn: The Captain's Cabin (Beach View)

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Furnished 1BR/1.5BA Luxury Condo, holiday rental in Chesapeake

Furnished 1BR/1.5BA Luxury Condo

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy 1 br near the Beach, holiday rental in Chesapeake

Cozy 1 br near the Beach

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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TennesSea | 635 ft from the beach, holiday rental in Chesapeake

TennesSea | 635 ft from the beach

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Climb aboard The Green Jewel, Sail away in your dreams!!, holiday rental in Chesapeake

Climb aboard The Green Jewel, Sail away in your dreams!!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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RVAcation | 98 ft from the beach | Private Pool, Hot Tub, holiday rental in Chesapeake

RVAcation | 98 ft from the beach | Private Pool, Hot Tub

6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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50 Steps from the Beach! WHY NOT Blend Business and Beach?!, holiday rental in Chesapeake

50 Steps from the Beach! WHY NOT Blend Business and Beach?!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sandswept Carriage House - Spacious Living at the Beach, holiday rental in Chesapeake

Sandswept Carriage House - Spacious Living at the Beach

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Virginia Beach House on Lake - 1 Blk to Coast, holiday rental in Chesapeake

Virginia Beach House on Lake - 1 Blk to Coast

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach Cottage Sand Suite, holiday rental in Chesapeake

Beach Cottage Sand Suite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Home Sweet Home Oceanfront, holiday rental in Chesapeake

Home Sweet Home Oceanfront

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Treehouse, holiday rental in Chesapeake

The Treehouse

2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Whole hse central VB, holiday rental in Chesapeake

Whole hse central VB

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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⭐️The Great Ghent Experience⭐️   *closes to beaches, holiday rental in Chesapeake

⭐️The Great Ghent Experience⭐️ *closes to beaches

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Chubb Lake Getaways, holiday rental in Chesapeake

Chubb Lake Getaways

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Pillow Talk - One Bedroom Apartment, Sleeps 4, holiday rental in Chesapeake

Pillow Talk - One Bedroom Apartment, Sleeps 4

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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'The Boom Boom Room', holiday rental in Chesapeake

'The Boom Boom Room'

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Virginia Beach Family  Home <1Mi to Golf Club, holiday rental in Chesapeake

NEW! Virginia Beach Family Home <1Mi to Golf Club

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Affordable Home 15 mins from the Oceanfront!!, holiday rental in Chesapeake

Spacious Affordable Home 15 mins from the Oceanfront!!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Modern Loft at Hunt Club Farm, holiday rental in Chesapeake

The Modern Loft at Hunt Club Farm

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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