We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chesapeake Holiday Apartments

List your property
Owner log in
Where to?
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 km
51 rentals in Chesapeake.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Peace on the lake, holiday rental in Chesapeake
Peace on the lake, holiday rental in Chesapeake
Peace on the lake, holiday rental in Chesapeake

Peace on the lake

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

The Bird’s Nest, holiday rental in Chesapeake
The Bird’s Nest, holiday rental in Chesapeake
The Bird’s Nest, holiday rental in Chesapeake

The Bird’s Nest

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Nestled in a quiet condo, just 15 minutes from VA Beach boardwalk. Sleeps five., holiday rental in Chesapeake
Nestled in a quiet condo, just 15 minutes from VA Beach boardwalk. Sleeps five., holiday rental in Chesapeake
Nestled in a quiet condo, just 15 minutes from VA Beach boardwalk. Sleeps five., holiday rental in Chesapeake

Nestled in a quiet condo, just 15 minutes from VA Beach boardwalk. Sleeps five.

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

NEW! ‘The Lucas:’ Cheery House w/ Fenced Backyard!, holiday rental in Chesapeake
NEW! ‘The Lucas:’ Cheery House w/ Fenced Backyard!, holiday rental in Chesapeake
NEW! ‘The Lucas:’ Cheery House w/ Fenced Backyard!, holiday rental in Chesapeake

NEW! ‘The Lucas:’ Cheery House w/ Fenced Backyard!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Comfortable Home (New Listing Discount), holiday rental in Chesapeake
Comfortable Home (New Listing Discount), holiday rental in Chesapeake
Comfortable Home (New Listing Discount), holiday rental in Chesapeake

Comfortable Home (New Listing Discount)

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

The Sparks Home! Relaxing Space + Lux Kitchen, holiday rental in Chesapeake
The Sparks Home! Relaxing Space + Lux Kitchen, holiday rental in Chesapeake
The Sparks Home! Relaxing Space + Lux Kitchen, holiday rental in Chesapeake

The Sparks Home! Relaxing Space + Lux Kitchen

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Cozy ranch style home located 20-25 minutes  from ocean front., holiday rental in Chesapeake
Cozy ranch style home located 20-25 minutes  from ocean front., holiday rental in Chesapeake
Cozy ranch style home located 20-25 minutes  from ocean front., holiday rental in Chesapeake

Cozy ranch style home located 20-25 minutes from ocean front.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Serene Spacious Suite - Unique Treehouse Theme, holiday rental in Chesapeake
Serene Spacious Suite - Unique Treehouse Theme, holiday rental in Chesapeake
Serene Spacious Suite - Unique Treehouse Theme, holiday rental in Chesapeake

Serene Spacious Suite - Unique Treehouse Theme

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Beautiful custom built home in the country, holiday rental in Chesapeake
Beautiful custom built home in the country, holiday rental in Chesapeake
Beautiful custom built home in the country, holiday rental in Chesapeake

Beautiful custom built home in the country

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

A Quiet Chesapeake Escape! Close to downtown, holiday rental in Chesapeake
A Quiet Chesapeake Escape! Close to downtown, holiday rental in Chesapeake
A Quiet Chesapeake Escape! Close to downtown, holiday rental in Chesapeake

A Quiet Chesapeake Escape! Close to downtown

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Save time - get the best Chesapeake rentals sent straight to your email!
Beautiful Waterfront Cottage near Downtown Norfolk- A Peaceful Secluded Paradise, holiday rental in Chesapeake
Beautiful Waterfront Cottage near Downtown Norfolk- A Peaceful Secluded Paradise, holiday rental in Chesapeake
Beautiful Waterfront Cottage near Downtown Norfolk- A Peaceful Secluded Paradise, holiday rental in Chesapeake

Beautiful Waterfront Cottage near Downtown Norfolk- A Peaceful Secluded Paradise

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

* NEW *Virginia Beach Newly remodel home A Perfect Getaway! 3 beds 2.5 baths, holiday rental in Chesapeake
* NEW *Virginia Beach Newly remodel home A Perfect Getaway! 3 beds 2.5 baths, holiday rental in Chesapeake
* NEW *Virginia Beach Newly remodel home A Perfect Getaway! 3 beds 2.5 baths, holiday rental in Chesapeake

* NEW *Virginia Beach Newly remodel home A Perfect Getaway! 3 beds 2.5 baths

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

�The Hidden Gem You’ll  this Mid Town Bungalow 25 minutes from the beach, holiday rental in Chesapeake
�The Hidden Gem You’ll  this Mid Town Bungalow 25 minutes from the beach, holiday rental in Chesapeake
�The Hidden Gem You’ll  this Mid Town Bungalow 25 minutes from the beach, holiday rental in Chesapeake

�The Hidden Gem You’ll this Mid Town Bungalow 25 minutes from the beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

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, holiday rental in Chesapeake
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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Best in the city for a place just like home with amusement park 45 minutes away., holiday rental in Chesapeake
Best in the city for a place just like home with amusement park 45 minutes away., holiday rental in Chesapeake
Best in the city for a place just like home with amusement park 45 minutes away., holiday rental in Chesapeake

Best in the city for a place just like home with amusement park 45 minutes away.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Well Priced VB Home only 15 mins from the Oceanfront!!, holiday rental in Chesapeake
Well Priced VB Home only 15 mins from the Oceanfront!!, holiday rental in Chesapeake
Well Priced VB Home only 15 mins from the Oceanfront!!, holiday rental in Chesapeake

Well Priced VB Home only 15 mins from the Oceanfront!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Live history, dont just visit!, holiday rental in Chesapeake
Live history, dont just visit!, holiday rental in Chesapeake
Live history, dont just visit!, holiday rental in Chesapeake

Live history, dont just visit!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Cozy Home!, holiday rental in Chesapeake
Cozy Home!, holiday rental in Chesapeake
Cozy Home!, holiday rental in Chesapeake

Cozy Home!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Bold & Bright Bungalow - Self Check In -  Quaint Street, holiday rental in Chesapeake
Bold & Bright Bungalow - Self Check In -  Quaint Street, holiday rental in Chesapeake
Bold & Bright Bungalow - Self Check In -  Quaint Street, holiday rental in Chesapeake

Bold & Bright Bungalow - Self Check In - Quaint Street

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

NEW! Virginia Beach Family  Home <1Mi to Golf Club, holiday rental in Chesapeake
NEW! Virginia Beach Family  Home <1Mi to Golf Club, holiday rental in Chesapeake
NEW! Virginia Beach Family  Home <1Mi to Golf Club, holiday rental in Chesapeake

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Welcome Military Welcome Civilians Welcome All, holiday rental in Chesapeake
Welcome Military Welcome Civilians Welcome All, holiday rental in Chesapeake
Welcome Military Welcome Civilians Welcome All, holiday rental in Chesapeake

Welcome Military Welcome Civilians Welcome All

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Adorable, detached, carriage guest house that is completely furnished., holiday rental in Chesapeake
Adorable, detached, carriage guest house that is completely furnished., holiday rental in Chesapeake
Adorable, detached, carriage guest house that is completely furnished., holiday rental in Chesapeake

Adorable, detached, carriage guest house that is completely furnished.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

The Charm of Old Towne Portsmouth, holiday rental in Chesapeake
The Charm of Old Towne Portsmouth, holiday rental in Chesapeake
The Charm of Old Towne Portsmouth, holiday rental in Chesapeake

The Charm of Old Towne Portsmouth

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Foxwell River Lodge S, holiday rental in Chesapeake
Foxwell River Lodge S, holiday rental in Chesapeake
Foxwell River Lodge S, holiday rental in Chesapeake

Foxwell River Lodge S

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Virginia beach newly remodeled Home centrally located Ocean front and Norfolk !!, holiday rental in Chesapeake
Virginia beach newly remodeled Home centrally located Ocean front and Norfolk !!, holiday rental in Chesapeake
Virginia beach newly remodeled Home centrally located Ocean front and Norfolk !!, holiday rental in Chesapeake

Virginia beach newly remodeled Home centrally located Ocean front and Norfolk !!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Spacious Affordable Home 15 mins from the Oceanfront!!, holiday rental in Chesapeake
Spacious Affordable Home 15 mins from the Oceanfront!!, holiday rental in Chesapeake
Spacious Affordable Home 15 mins from the Oceanfront!!, holiday rental in Chesapeake

Spacious Affordable Home 15 mins from the Oceanfront!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Modern Oasis - Entire Luxury Stay Close to Beaches, holiday rental in Chesapeake
Modern Oasis - Entire Luxury Stay Close to Beaches, holiday rental in Chesapeake
Modern Oasis - Entire Luxury Stay Close to Beaches, holiday rental in Chesapeake

Modern Oasis - Entire Luxury Stay Close to Beaches

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Historic stay in Olde Town Portsmouth with Instagram worthy details!, holiday rental in Chesapeake
Historic stay in Olde Town Portsmouth with Instagram worthy details!, holiday rental in Chesapeake
Historic stay in Olde Town Portsmouth with Instagram worthy details!, holiday rental in Chesapeake

Historic stay in Olde Town Portsmouth with Instagram worthy details!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Cozy Colony Nest, holiday rental in Chesapeake
Cozy Colony Nest, holiday rental in Chesapeake
Cozy Colony Nest, holiday rental in Chesapeake

Cozy Colony Nest

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

S&N Novah Suite, holiday rental in Chesapeake
S&N Novah Suite, holiday rental in Chesapeake
S&N Novah Suite, holiday rental in Chesapeake

S&N Novah Suite

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Cozy bungalow - easy reach to great eateries, shopping and beaches, holiday rental in Chesapeake
Cozy bungalow - easy reach to great eateries, shopping and beaches, holiday rental in Chesapeake
Cozy bungalow - easy reach to great eateries, shopping and beaches, holiday rental in Chesapeake

Cozy bungalow - easy reach to great eateries, shopping and beaches

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Family friendly! 3 bd/2 ba, full house, sleeps 8, holiday rental in Chesapeake
Family friendly! 3 bd/2 ba, full house, sleeps 8, holiday rental in Chesapeake
Family friendly! 3 bd/2 ba, full house, sleeps 8, holiday rental in Chesapeake

Family friendly! 3 bd/2 ba, full house, sleeps 8

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Quiet, Clean and Cozy Private Suite, holiday rental in Chesapeake
Quiet, Clean and Cozy Private Suite, holiday rental in Chesapeake
Quiet, Clean and Cozy Private Suite, holiday rental in Chesapeake

Quiet, Clean and Cozy Private Suite

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

S&N Remote Suites Serenity Suite, holiday rental in Chesapeake
S&N Remote Suites Serenity Suite, holiday rental in Chesapeake
S&N Remote Suites Serenity Suite, holiday rental in Chesapeake

S&N Remote Suites Serenity Suite

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Private 1 Bed Apt - Historic Olde Towne Portsmouth, holiday rental in Chesapeake
Private 1 Bed Apt - Historic Olde Towne Portsmouth, holiday rental in Chesapeake
Private 1 Bed Apt - Historic Olde Towne Portsmouth, holiday rental in Chesapeake

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

The Enchantment of Old Towne Portsmouth - Suite 2, holiday rental in Chesapeake
The Enchantment of Old Towne Portsmouth - Suite 2, holiday rental in Chesapeake
The Enchantment of Old Towne Portsmouth - Suite 2, holiday rental in Chesapeake

The Enchantment of Old Towne Portsmouth - Suite 2

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

The Enchantment of Old Towne Portsmouth - Suite 1, holiday rental in Chesapeake
The Enchantment of Old Towne Portsmouth - Suite 1, holiday rental in Chesapeake
The Enchantment of Old Towne Portsmouth - Suite 1, holiday rental in Chesapeake

The Enchantment of Old Towne Portsmouth - Suite 1

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

The Allure of Old Towne Portsmouth - Suite 2, holiday rental in Chesapeake
The Allure of Old Towne Portsmouth - Suite 2, holiday rental in Chesapeake
The Allure of Old Towne Portsmouth - Suite 2, holiday rental in Chesapeake

The Allure of Old Towne Portsmouth - Suite 2

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

3Blocks from the waterfront and Pavillion 1Bedroom Private Suite Cloud Room, holiday rental in Chesapeake
3Blocks from the waterfront and Pavillion 1Bedroom Private Suite Cloud Room, holiday rental in Chesapeake
3Blocks from the waterfront and Pavillion 1Bedroom Private Suite Cloud Room, holiday rental in Chesapeake

3Blocks from the waterfront and Pavillion 1Bedroom Private Suite Cloud Room

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Evergreen house…, holiday rental in Chesapeake
Evergreen house…, holiday rental in Chesapeake
Evergreen house…, holiday rental in Chesapeake

Evergreen house…

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

After Game Getaway, holiday rental in Chesapeake
After Game Getaway, holiday rental in Chesapeake
After Game Getaway, holiday rental in Chesapeake

After Game Getaway

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

The Allure of Old Towne Portsmouth - Suite 1, holiday rental in Chesapeake
The Allure of Old Towne Portsmouth - Suite 1, holiday rental in Chesapeake
The Allure of Old Towne Portsmouth - Suite 1, holiday rental in Chesapeake

The Allure of Old Towne Portsmouth - Suite 1

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Clean spacious home near Sentara Hospital, holiday rental in Chesapeake
Clean spacious home near Sentara Hospital, holiday rental in Chesapeake
Clean spacious home near Sentara Hospital, holiday rental in Chesapeake

Clean spacious home near Sentara Hospital

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

The Morgan Trail House, holiday rental in Chesapeake
The Morgan Trail House, holiday rental in Chesapeake
The Morgan Trail House, holiday rental in Chesapeake

The Morgan Trail House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Love Boat Adventurer, holiday rental in Chesapeake
Love Boat Adventurer, holiday rental in Chesapeake
Love Boat Adventurer, holiday rental in Chesapeake

Love Boat Adventurer

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Private single family home with a natural wooded setting providing much privacy., holiday rental in Chesapeake
Private single family home with a natural wooded setting providing much privacy., holiday rental in Chesapeake
Private single family home with a natural wooded setting providing much privacy., holiday rental in Chesapeake

Private single family home with a natural wooded setting providing much privacy.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Lovely 3- bedroom home with yard and a game room., holiday rental in Chesapeake
Lovely 3- bedroom home with yard and a game room., holiday rental in Chesapeake
Lovely 3- bedroom home with yard and a game room., holiday rental in Chesapeake

Lovely 3- bedroom home with yard and a game room.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

3 BR 2 BA Bungalow in a quiet area near DT/Hwy264, holiday rental in Chesapeake
3 BR 2 BA Bungalow in a quiet area near DT/Hwy264, holiday rental in Chesapeake
3 BR 2 BA Bungalow in a quiet area near DT/Hwy264, holiday rental in Chesapeake

3 BR 2 BA Bungalow in a quiet area near DT/Hwy264

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

Oak St. Oasis, holiday rental in Chesapeake
Oak St. Oasis, holiday rental in Chesapeake
Oak St. Oasis, holiday rental in Chesapeake

Oak St. Oasis

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
Check-in
Check-out
Payment Protection

Charming 3 bedroom house on Cul-de-sac, holiday rental in Chesapeake
Charming 3 bedroom house on Cul-de-sac, holiday rental in Chesapeake
Charming 3 bedroom house on Cul-de-sac, holiday rental in Chesapeake

Charming 3 bedroom house on Cul-de-sac

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Stayz.com.au logo
Check-in
Check-out

PreviousNext
12