Chesapeake Holiday Homes
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Chesapeake

Spacious oceanfront house w/beach access, decks, grill & free WIFI

Captain’s Suite Beach Condo Near Rudee Inlet

Oceanfront home “Sea Watch” ~~brand new pool

Your own private beach with this charming 3-bedroom beachfront house!

Inviting oceanfront home with amazing views, private pool & deck

Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.

Serenity on the Bay-Complimentary Sunrise & Sunset Views

Oceanfront home with private pool, hot tub, outdoor bar, theater room, game room

Oceanfront 7BR Home w/ Pool, Hot Tub. Sleeps 20

Charming Tiny Cottage

Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views

Dog-Friendly, Ocean View Beach Retreat w/Private Outdoor Pool, Decks & A/C
Holiday Accommodation Chesapeake
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chesapeake are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chesapeake itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chesapeake holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chesapeake, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chesapeake with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Chesapeake Holiday Homes essential information
Accommodation | 1415 Holiday Homes |
|---|---|
Lowest Price | NZ$109 |
Highest Price | NZ$207 |
Popular accommodation | Spacious oceanfront house w/beach access, decks, grill & free WIFI, Captain’s Suite Beach Condo Near Rudee Inlet, Oceanfront home “Sea Watch” ~~brand new pool, Your own private beach with this charming 3-bedroom beachfront house!, Inviting oceanfront home with amazing views, private pool & deck, Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk., Serenity on the Bay-Complimentary Sunrise & Sunset Views, Oceanfront home with private pool, hot tub, outdoor bar, theater room, game room, Oceanfront 7BR Home w/ Pool, Hot Tub. Sleeps 20, Charming Tiny Cottage, Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views, Dog-Friendly, Ocean View Beach Retreat w/Private Outdoor Pool, Decks & A/C |
Top trending hotels in Chesapeake

Comfort Suites Chesapeake - Norfolk
Top cities with Holiday Homes
More Holiday Homes
More accommodations in Chesapeake
^Eligibility requirements and conditions apply







