Holiday Homes in Middlesex County

Compare and save

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Featured Holiday Homes in Middlesex County

Cozy Bungalow Just Minutes From Mystic, Westerly Beaches, Boating And Casinos! 1 Bedroom Bungalow by RedAwning
Bungalow, 1 Bedroom | Exterior

Cozy Bungalow Just Minutes From Mystic, Westerly Beaches, Boating And Casinos! 1 Bedroom Bungalow by RedAwning

3.5 star property
Cozy Bungalow Just Minutes From Mystic, Westerly Beaches, Boating And Casinos! 1 Bedroom Bungalow by RedAwning
Room-plaid Room 3min From Yale Univ
Shared Dormitory, 1 Bedroom | Outdoor dining

Room-plaid Room 3min From Yale Univ

3.0 star property
10.0 out of 10, Exceptional, (1)
"The owner is great and made great accommodations for our stay, the price was wonderful. The neighborhood maybe wasent the nicest but thats kinda out of his control."
Room-plaid Room 3min From Yale Univ
Mattituck Luxury Estate
Luxury House, Private Bathroom (Mattituck Luxury Estate) | Shared kitchen

Mattituck Luxury Estate

3.0 star property
Mattituck Luxury Estate
Bluffside Cove by Rove Beachfront w Pool Sauna
House | Internet

Bluffside Cove by Rove Beachfront w Pool Sauna

2.0 star property
Bluffside Cove by Rove Beachfront w Pool Sauna
Meadowood Manor by Rovetravel Heated Pool
House | Internet

Meadowood Manor by Rovetravel Heated Pool

2.0 star property
Meadowood Manor by Rovetravel Heated Pool
Sunset Villa by Rove Beachfront w Deck Pool
House | Internet

Sunset Villa by Rove Beachfront w Deck Pool

2.0 star property
Sunset Villa by Rove Beachfront w Deck Pool
Sandpoint by Rove Travel Modern 5BR w Pool
House | Internet

Sandpoint by Rove Travel Modern 5BR w Pool

2.0 star property
Sandpoint by Rove Travel Modern 5BR w Pool
Sage and Madison House - Hatfield Suite - 3rd Floor
Apartment, Multiple Beds (Sage and Madison House - Hatfield Sui) | Living room

Sage and Madison House - Hatfield Suite - 3rd Floor

3.5 star property
Sage and Madison House - Hatfield Suite - 3rd Floor
Coves Bay Beauty
House, Multiple Beds (Coves Bay Beauty) | Living area | TV, fireplace

Coves Bay Beauty

4.0 star property
Coves Bay Beauty
Walkable Home in Mystic Historic District
Room | Terrace/patio

Walkable Home in Mystic Historic District

3.5 star property
Walkable Home in Mystic Historic District
Escape by Gardiners Bay
House, Multiple Beds (Escape by Gardiners Bay) | Private kitchen | Microwave, toaster, blender

Escape by Gardiners Bay

3.5 star property
Escape by Gardiners Bay
Hog Creek Breeze
House, Multiple Beds (Hog Creek Breeze) | Pool | Outdoor pool, a heated pool

Hog Creek Breeze

2.0 star property
Hog Creek Breeze
Solara Resort - 1617 Nassau Point Trial
Villa, 6 Bedrooms | Aerial view

Solara Resort - 1617 Nassau Point Trial

2.5 star property
Solara Resort - 1617 Nassau Point Trial
North Fork Beach Bungalow Vineyards, Farmstands, Kayaks, Bikes
Beach | On the beach

North Fork Beach Bungalow Vineyards, Farmstands, Kayaks, Bikes

3.5 star property
North Fork Beach Bungalow Vineyards, Farmstands, Kayaks, Bikes
Wonderful in Springs
House, Multiple Beds (Wonderful in Springs) | Private kitchen

Wonderful in Springs

3.5 star property
Wonderful in Springs
Springs Panorama
House, Multiple Beds (Springs Panorama) | Private kitchen | Fridge, microwave, dishwasher, toaster

Springs Panorama

3.5 star property
Springs Panorama
East Hampton Springs Haven
House, 2 Queen Beds (East Hampton Springs Haven) | Property grounds

East Hampton Springs Haven

2.0 star property
East Hampton Springs Haven
North Fork Waterfront Wonder
House, Multiple Beds (North Fork Waterfront Wonder) | Private kitchen

North Fork Waterfront Wonder

2.0 star property
North Fork Waterfront Wonder
Greenport Getaway
House, Multiple Beds (Greenport Getaway) | Private kitchen

Greenport Getaway

3.5 star property
Greenport Getaway
Que Luxury Camper Ct
Interior

Que Luxury Camper Ct

2.0 star property
Que Luxury Camper Ct
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlesex County Hotel Reviews

Spark by Hilton Mystic Groton

Spark by Hilton Mystic Groton

10/10 Excellent
"Love it"
Larry 2-night trip
Posted 18 hours ago
Spark by Hilton Mystic Groton