A coastal town with a lighthouse, houses, and a river.

Private Holiday Homes in Middlesex County

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Our top choices for Middlesex County holiday homes

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

Cozy Bungalow Just Minutes From Mystic, Westerly Beaches, Boating And Casinos! 1 Bedroom Bungalow by RedAwning
3.5 star property
Mystic
10.0 out of 10, Exceptional, (1 review)
"We booked because the property was pet friendly. The owners have a large property and we did not see them until we checked out. We had our privacy in a secluded area, with a private deck and area to walk our dog. "
United States
Andrew Paul
Cozy Bungalow Just Minutes From Mystic, Westerly Beaches, Boating And Casinos! 1 Bedroom Bungalow by RedAwning

2. Room-plaid Room 3min From Yale Univ

Room-plaid Room 3min From Yale Univ
3.0 star property
Newhallville
10.0 out of 10, Exceptional, (1 review)
"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."
United States
Colby
Room-plaid Room 3min From Yale Univ

3. Connecticut Beach Home

Connecticut Beach Home
2.0 star property
Old Lyme
Connecticut Beach Home

4. Sunset Villa by Rove Beachfront w Deck Pool

Sunset Villa by Rove Beachfront w Deck Pool
2.0 star property
Sag Harbor
Sunset Villa by Rove Beachfront w Deck Pool

5. Solara Resort - 1617 Nassau Point Trial

Solara Resort - 1617 Nassau Point Trial
2.5 star property
Cutchogue
Solara Resort - 1617 Nassau Point Trial

6. Hollow Tree Hideaway

Hollow Tree Hideaway
3.5 star property
East Hampton
Hollow Tree Hideaway

7. Sage and Madison House - Hatfield Suite - 3rd Floor

Sage and Madison House - Hatfield Suite - 3rd Floor
3.5 star property
Sag Harbor
Sage and Madison House - Hatfield Suite - 3rd Floor

8. East Hampton Hideaway

East Hampton Hideaway
3.5 star property
East Hampton
East Hampton Hideaway

9. Sag Harbor Village Sensation

Sag Harbor Village Sensation
3.0 star property
Sag Harbor
Sag Harbor Village Sensation

10. Meadowood Manor by Rovetravel Heated Pool

Meadowood Manor by Rovetravel Heated Pool
2.0 star property
Sag Harbor
Meadowood Manor by Rovetravel Heated Pool

11. Waterfront Modern in East Hampton

Waterfront Modern in East Hampton
3.5 star property
Lafarges Landing
Waterfront Modern in East Hampton

12. Sammys Beach Stately Retreat

Sammys Beach Stately Retreat
3.5 star property
East Hampton
Sammys Beach Stately Retreat

13. Villa Lilith

Villa Lilith
4.0 star property
Clearwater Beach
Villa Lilith

14. Walkable Home in Mystic Historic District

Walkable Home in Mystic Historic District
3.5 star property
Mystic River Historic District
Walkable Home in Mystic Historic District

15. North Fork Beach Bungalow Vineyards, Farmstands, Kayaks, Bikes

North Fork Beach Bungalow Vineyards, Farmstands, Kayaks, Bikes
3.5 star property
Mattituck
North Fork Beach Bungalow Vineyards, Farmstands, Kayaks, Bikes

16. Wonderful in Springs

Wonderful in Springs
3.5 star property
East Hampton
Wonderful in Springs

17. Noyack Bay Beauty

Noyack Bay Beauty
3.5 star property
Sag Harbor
Noyack Bay Beauty

18. Wine Country Contemporary

Wine Country Contemporary
4.0 star property
Mattituck
Wine Country Contemporary

19. Escape by Gardiners Bay

Escape by Gardiners Bay
3.5 star property
East Hampton
Escape by Gardiners Bay

20. Beach Road Retreat

Beach Road Retreat
3.0 star property
Lafarges Landing
Beach Road Retreat
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

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Middlesex County Private Holiday Homes information

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2
Accommodation
39 Private Holiday Homes
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