Deep River Vacations from $619
Book a Hotel + Flight or Car together to unlock savings
The Latest Deep River Vacation Packages
- New Haven Hotel
Oct 24 - Oct 29New Haven Hotel + Flight
Downtown New Haven5 nights3.5 star property9.2/10 - Wonderful (2,267 reviews)"Super clean, beds were amazing, rooms quiet, fitness center nice!"Reviewed August 6, 2026Roundtrip • Tampa (TPA) - New Haven (HVN)TPA - HVN • Nonstop HVN - TPA • Nonstop - Solano Inn
Oct 8 - Oct 13Solano Inn + Flight
Portland5 nights2.5 star property8.4/10 - Very Good (262 reviews)Roundtrip • San Juan (SJU) - Hartford (BDL)SJU - BDL • Nonstop BDL - SJU • Nonstop$957$686found 1 day agoper traveler - Landing Apartments New Haven Near Dixwell
Oct 24 - Oct 29Landing Apartments New Haven Near Dixwell + Flight
Newhallville5 nights3.0 star property2.0/10 - (1 review)"The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host."Reviewed May 25, 2026Roundtrip • Tampa (TPA) - New Haven (HVN)TPA - HVN • Nonstop HVN - TPA • Nonstop - Beechmont - Perfect for Family Retreat!
Oct 24 - Oct 29Beechmont - Perfect for Family Retreat! + Flight
North End5 nights5.0 star propertyRoundtrip • Tampa (TPA) - New Haven (HVN)TPA - HVN • Nonstop HVN - TPA • Nonstop - Omni New Haven Hotel at Yale
Oct 24 - Oct 29Omni New Haven Hotel at Yale + Flight
Downtown New Haven5 nights4.0 star property8.6/10 - Excellent (1,075 reviews)"Great stay! Would recommend highly."Reviewed August 5, 2026Roundtrip • Tampa (TPA) - New Haven (HVN)TPA - HVN • Nonstop HVN - TPA • Nonstop
Where to stay in Deep River
Deep River Center
While there might not be top attractions in Deep River Center, you can explore the larger area and discover places like Chester Creek Marina and Ivoryton Playhouse.
Deep River Hotel Deals
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook"Decent location for a 1 night stopover, right off the freeway. The front desk help was excellent. The gym was pretty much useless, but the breakfast buffet was very good. The hotel was very quiet."
"Very clean room, some hidden costs added during check in. Resort fee tax and town or state"
Econo Lodge Inn & Suites Old Saybrook Westbrook
Econo Lodge Inn & Suites Old Saybrook Westbrook"Room was clean and comfortable, did not like the view from the window."
Holiday Inn Express Branford-New Haven by IHG
Holiday Inn Express Branford-New Haven by IHG"Great location"
Super 8 by Wyndham Old Saybrook
Super 8 by Wyndham Old SaybrookFrequently Asked Questions
How much does a Deep River vacation package cost?
You'll find cheap prices from $619 on Expedia for your Deep River break. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Deep River costs.
What are the cheapest months to go to Deep River?
If you're looking to score a cheap Deep River vacation package, consider traveling in December, January and February. You'll generally find better rates on flights and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Deep River?
The ideal length for your Deep River vacation depends on what you'd like to see. Typically, a few days to a week will give you time to go to all the leading sights and explore some hidden spots along the way.
How to find the best Deep River package deals?
Use Expedia's handy filters to find some tempting Deep River package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Deep River package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Deep River vacation as a package?
You can enjoy significant savings on your Deep River escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Deep River?
Secure amazing discounts by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Deep River trip.
Does Expedia offer Book Now, Pay Later Deep River vacation packages?
Your Deep River break is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to allow you that extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.