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Holiday Rentals and Homes in Chesapeake, VA

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    1 / 17
    Chesapeake
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    1 / 19
    5 of 5 stars (13) Excellent
    Chesapeake
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    The following rentals are within 15 kilometers of Chesapeake, Virginia.

    1 / 31
    5 of 5 stars (1) Excellent
    Norfolk
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 27
    4.5 of 5 stars (3) Very good
    Norfolk
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Housekeeping...
    • Patio
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    AN IDYLLIC locale for family excursions, weddings & receptions and/or a relaxing respite from the rat race! Imagine an expansive retreat reminiscent of Frank Sinatra, Dean Martin & Sammy Davis Jr.! Wiseacre Estate is a whimsical 4000sf Frank Lloyd Wright-inspired property built in 1962. Enjoy... View all property information
    Location Information
    Norfolk, Virginia
    4 of 5 stars Reviewed 29 June 2016
    Chuck is an excellent host and enjoyable to stay with. Great location for access to Virginia Beach and Newport News areas. Great to go to patio in mornings and evenings to relax...
    5 of 5 stars Reviewed 14 May 2015
    Wiseacre Estate was beautiful, spacious, had amazing views (great sunrises and sunsets), and had all of the amenities needed (kitchen, laundry, living, bathroom, etc.). Our host...
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    1 / 22
    5 of 5 stars (1) Excellent
    Norfolk
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Patio
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Balcony
    • Housekeeping...
    • Waterfront
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    About this property
    Imagine an expansive retreat reminiscent of Frank Sinatra, Dean Martin & Sammy Davis Jr.! Wiseacre Estate is a whimsical 4000sf Frank Lloyd Wright-inspired property built in 1962. Enjoy the tranquility of this authentic Mid-Century Modern home... with a cavernous 650sf great room (20-foot... View all property information
    Location Information
    Norfolk, Virginia
    5 of 5 stars Reviewed 5 August 2015
    My extended family recently (July 26-Aug 2) converged on the Norfolk area for vacation. We rented this home, and it was the best decision we could have made for accommodations. It...
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    1 / 4
    Norfolk
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Newly Remodeled two bedroom home in Colonial Place....historic neighborhood in Norfolk. Close to Old Dominion University and Norfolk Naval Base. Walking distance to local restaurants, coffee shops etc. Beautifully decorated with hardwood floors and all new furniture. We are excited to host... View all property information
    Location Information
    Norfolk, Virginia
    1 / 29
    Norfolk
    4 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Waterfront home, close to Williamsburg, the historic triangle, or Virginia Beach. There is a beach on site as well as a 2nd beach that is 7 miles long, AND not crowded. 4 bedroom with lots of parking, (no events sorry). Home has large waterfront deck. Large dining table, fireplace for winter.... View all property information
    Location Information
    Norfolk, Virginia
    1 / 14
    Norfolk
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Satellite TV
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Coastal Virginia at it's best! This beautiful, big beach house sits right on the dune and Chesapeake Bay! With 5 bedrooms (1 King, 5 queen, 4 baths, two dining room tables seating 12 plus bar seating, and fully equipped kitchen this is a perfect family get together! The porches, decks and... View all property information
    Location Information
    Norfolk, Virginia
    1 / 19
    4 of 5 stars (1) Very good
    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Internet Access
    • Washer
    • Ocean Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful Fully updated beach house on Ocean View Ave in Norfolk, VA for rent. Just steps from the ocean / beach. ALL utilities included, water, trash, electricity, cable, Internet. Beach house is completely furnished. No Pets, No Smoking. MOVE IN IMMEDIATELY. The ad will be removed once the beach... View all property information
    Location Information
    Norfolk, Virginia
    4 of 5 stars Reviewed 26 June 2016
    Great little apartment! Very clean, modern and secure! Private driveway and keycode to get in, so no worries about losing keys. My husband and I stayed here with our 3 young...
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    1 / 28
    Norfolk
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Waterfront
    • Balcony
    • Patio
    • Secure Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Cozy 2-BR/1-BA 1924 Bungalow waterfront property with deep dock and pier access. Walking distance to neighborhood shops and restaurants. Within walking distance to ODU Campus. Full eastern waterfront exposure as you awaken to sunlit bedroom to plan your day on the water. Use of (2) kayaks to... View all property information
    Location Information
    Norfolk, Virginia
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    1 / 33
    Norfolk
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • DVD Player
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Exquisitely furnished 1bdrm New York loft style luxury condo with interior brick, and Brazilian hardwood floors throughout. Stainless steel island with industrial grade updraft and ventilation system. Granite counters throughout kitchen and master bath. Flat screen 3-D television with your favorite... View all property information
    Location Information
    Norfolk, Virginia
    1 / 18
    Norfolk
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Grill
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Ocean Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come enjoy our beautiful five bedroom home within steps to the Chesapeake Bay. Huge master bedroom and expansive views of the bay. Opening living space, with three large out door decks. Please visit Vacation Rental By Owner to book. Property number 717981. Fish, Hunt for Shells, or just walk... View all property information
    Location Information
    Norfolk, Virginia
    1 / 8
    Norfolk
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Terrace
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Looking for a really nice beach house to stay in? Try the Pink House on the Bay! 4 bdrms (3 queen, 1 full beds) 2 full bath, fully equipped kitchen. The porches, decks and balcony overlook the bay. Fireplace - both wood burning and gas is available (for our winter guests) Outside is a small,... View all property information
    Location Information
    Norfolk, Virginia
    1 / 14
    Portsmouth
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Waterfront
    • Housekeeping...
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Waterfront self-cater suite over an unattached garage in quiet family-friendly neighborhood. Efficiency offers queen bed, bath w/shower, desk, sofa, chair & wardrobe. Kitchenette offers small fridge, microwave, toaster oven & coffee. Close to hospital, marina & downtown. Home is located in the... View all property information
    Location Information
    Portsmouth, Virginia
    1 / 24
    Norfolk
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Come visit this lovely bayside Norfolk vacation rental townhome, ideally settled within close walking distance of the Chesapeake Bay. With 3 bedrooms, 3.5 baths, and a prime location near ample major Virginia attractions, this home is sure to please! Featuring 2,437 square feet of beautifully... View all property information
    Location Information
    Norfolk, Virginia