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Vacation Homes in Middlesex County

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Middlesex County vacation homes

Terrace/patio

Bay Front Small Contemporary

Bay Front Small Contemporary
Reedville
9.8 out of 10, Exceptional, (119 reviews)
"Absolutely love this place!"
United States
Robin S.
Bay Front Small Contemporary
Interior

Cozy cottage on the Chesapeake Bay

Cozy cottage on the Chesapeake Bay
Hallieford
9.8 out of 10, Exceptional, (56 reviews)
"Great house. Beautiful location. We had everything what we need. "
United States
Beata S.
Cozy cottage on the Chesapeake Bay
Terrace/patio

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE
Cobbs Creek
9.6 out of 10, Exceptional, (27 reviews)
"Good value, good communication. Access to great kayaking. Would stay here again."
United States
Kurt N.
Kimary Cove - Waterfront Relaxation and NO CLEANING FEE
Property grounds

Modern Waterfront Retreat on 5 Acres w Pier, Kayaks, Fishing & Crabbing

Modern Waterfront Retreat on 5 Acres w Pier, Kayaks, Fishing & Crabbing
Lottsburg
9.0 out of 10, Wonderful, (16 reviews)
"We were visiting family nearby and had a great visit! Property was clean and well appointed. The kids loved the air hockey table and board games. "
United States
Tracey H.
Modern Waterfront Retreat on 5 Acres w Pier, Kayaks, Fishing & Crabbing
Exterior

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
Reedville
10.0 out of 10, Exceptional, (73 reviews)
"The views from the dock are beautiful and there is a lot to do at the house! I will definitely rebook when visiting the area."
United States
Brooke
Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
Interior

Little Bay Waterfront Retreat

Little Bay Waterfront Retreat
White Stone
9.8 out of 10, Exceptional, (74 reviews)
"Great location and lovdlh home!"
United States
Linda O.
Little Bay Waterfront Retreat
TV

Chesapeake Bay Escape

Chesapeake Bay Escape
Exmore
10.0 out of 10, Exceptional, (1 review)
"La maison est magnifique et parfaitement équipée. Nous avons bien profité du quai pour pecher le crabe et y prendre un café. Endroit très tranquille."
Canada
VERUSKA
Chesapeake Bay Escape
Smart TV, fireplace, table tennis, books

Serenity on the Rappahannock

Serenity on the Rappahannock
White Stone
10.0 out of 10, Exceptional, (17 reviews)
"Great house and location. Stunning view. "
United States
Tim B.
Serenity on the Rappahannock
Outdoor dining

Irvington's BEST WATERFRONT EXPERIENCE!. Walk to Tides Inn & Irvington shops.

Irvington's BEST WATERFRONT EXPERIENCE!. Walk to Tides Inn & Irvington shops.
Irvington
10.0 out of 10, Exceptional, (126 reviews)
"Great for family gatherings"
United States
Amy N.
Irvington's BEST WATERFRONT EXPERIENCE!. Walk to Tides Inn & Irvington shops.
WiFi (free), bed sheets

Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.8 out of 10, Exceptional, (22 reviews)
"Great place "
United States
Myranda R.
The price is AED 415
AED 993 total
includes taxes & fees
27 Jul - 28 Jul
Newly updated 3 bedroom cottage with Solo Stove fire pit
Coffee/tea maker, fridge, microwave, oven

Welcome to this Waterfront Home with Amazing Views

Welcome to this Waterfront Home with Amazing Views
Gloucester
10.0 out of 10, Exceptional, (38 reviews)
"This was the most delightful property we have stayed at. The house was so cute and the owner thought of everything and more to make our stay exceptional. "
United States
Tami C.
Welcome to this Waterfront Home with Amazing Views
Beach nearby

BAYHAMAS ✌️❤️ Beachfront Home 3 Bedrooms-Private-White Stone- Sauna-Dock

BAYHAMAS ✌️❤️ Beachfront Home 3 Bedrooms-Private-White Stone- Sauna-Dock
White Stone
9.2 out of 10, Wonderful, (19 reviews)
"This was a great place for our family get away. Your right on a beach which was great for kids. Beautiful views, quiet and relaxing."
United States
Anonymous traveler
BAYHAMAS ✌️❤️ Beachfront Home 3 Bedrooms-Private-White Stone- Sauna-Dock
Desk, iron/ironing board, free WiFi, bed sheets

Belle Haven - High Speed internet, walk to town

Belle Haven - High Speed internet, walk to town
Kilmarnock
10.0 out of 10, Exceptional, (38 reviews)
"Great cottage, beautiful place to stay at"
United States
Darren W.
The price is AED 613
AED 1,275 total
includes taxes & fees
28 Jul - 29 Jul
Belle Haven - High Speed internet, walk to town
Interior

Private Waterfront Retreat on Locklie’s Creek w/Dock + Wildlife views

Private Waterfront Retreat on Locklie’s Creek w/Dock + Wildlife views
Topping
10.0 out of 10, Exceptional, (1 review)
"Retreat is the right word to describe this home. Such a peaceful, beautiful place! We had a great time kayaking and fishing off the dock. We were sad to leave!"
United States
Dawn C.
Private Waterfront Retreat on Locklie’s Creek w/Dock + Wildlife views
Beach nearby

Charming 2-bedroom house on the Chesapeake Bay

Charming 2-bedroom house on the Chesapeake Bay
White Stone
9.6 out of 10, Exceptional, (30 reviews)
"We absolutely loved our peaceful stay here. This house had so much character and was so cozy for our Chesapeake Bay vacation ! There is a small town close by (7 minute drive) with amazing food options. The beach is a two minute drive from the home. Very relaxing stay , host was very responsive. Linens were fresh and house had EVERYTHING you needed. Very accommodating stay - thank you!"
United States
Kaitlin
Charming 2-bedroom house on the Chesapeake Bay
Exterior

Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!

Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
Bohannon
10.0 out of 10, Exceptional, (199 reviews)
"Clean, beautiful home! Pet friendly! Hosts were so kind and helpful! "
United States
Erica F.
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
Property grounds

Waterfront retreat w/pool, dock & fire pit in Urbanna. BRING YOUR BOAT!

Waterfront retreat w/pool, dock & fire pit in Urbanna. BRING YOUR BOAT!
Urbanna
10.0 out of 10, Exceptional, (4 reviews)
"Owner and house were amazing! Gorgeous property on the rivah!"
United States
Daniel S.
Waterfront retreat w/pool, dock & fire pit in Urbanna. BRING YOUR BOAT!
Outdoor dining

Pet-Friendly Waterfront Retreat w/ Private Dock on Virginia’s Eastern Shore

Pet-Friendly Waterfront Retreat w/ Private Dock on Virginia’s Eastern Shore
Exmore
10.0 out of 10, Exceptional, (16 reviews)
"Absolutely wonderful stay at the Ripple.It's a bit off the beaten path but if you're looking for peace and tranquility, look no further."
United States
Sammi-jo S.
Pet-Friendly Waterfront Retreat w/ Private Dock on Virginia’s Eastern Shore
Interior

The Mill Camp offers comfortable and affordable accommodations. Pet Friendly!

The Mill Camp offers comfortable and affordable accommodations. Pet Friendly!
Mattaponi
9.8 out of 10, Exceptional, (29 reviews)
"We had a great stay! "
United States
Stephanie H.
The Mill Camp offers comfortable and affordable accommodations. Pet Friendly!
Beach nearby

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Irvington
9.6 out of 10, Exceptional, (187 reviews)
"This was our 2nd stay here and we look forward to returning. "
United States
Katie L.
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlesex County Hotel Reviews

Great Wolf Lodge Williamsburg

Great Wolf Lodge Williamsburg

8/10 Good
"Rooms were lovely. Water park was enjoyable my daughter had fun. A bit too crowdy for my taste especially seeing its an indoor space."
Shana Kay 1-night trip
Posted 4 hours ago
Great Wolf Lodge Williamsburg