Vacation rentals in Deep River

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Deep River

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Lyme

4.97 out of 5 average rating, 185 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023 and featured in “Only In Your State” titled “This Riverfront House Will Be Your New Favorite” February 2024 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

Sep 28 – Oct 5

ﺩ.ﺇ1,253 per night
Guest favorite

Apartment in Chester

4.95 out of 5 average rating, 309 reviews

Chester Village 'Pied-à-terre' above art gallery

If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled living room w/ high ceilings, a private bedroom in back w/ large private deck overlooking Pattaconk Brook. Our place is a gem, and set up for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT! NEW! Winter weekdays - ONE night stays are now available - message us!

Dec 20 – 27

ﺩ.ﺇ748 per night
Guest favorite

Home in Chester

4.98 out of 5 average rating, 193 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

Rated one of the top 70 airbnb's near NYC on the online mag "Curbed". Featured on EarthxTV "House of What" series. Over 10 years of craftsmanship went into creating a work of art using more than 80% recycled materials. Known locally as "The Recycle House," this is the perfect place to stay to explore shops and galleries in downtown Chester - just steps away. When you are done shopping, come back and relax in the zen-like garden overlooking a waterfall or curl up inside by the fire place.

May 3 – 10

ﺩ.ﺇ1,213 per night

Popular amenities for Deep River vacation rentals

Stay near Deep River's top sights

Essex Steam Train & Riverboat60 locals recommend
The Griswold Inn49 locals recommend
Connecticut River Museum38 locals recommend
Scotch Plains Tavern13 locals recommend
Red House6 locals recommend
Adams Hometown Market8 locals recommend

Other great vacation rentals in Deep River

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 48 reviews

Cozy Shoreline Getaway

May 25 – Jun 1

ﺩ.ﺇ445 per night
Guest favorite

Guesthouse in Chester

5.0 out of 5 average rating, 41 reviews

Delightful Cottage in Charming Chester

Nov 12 – 19

ﺩ.ﺇ798 per night
Guest favorite

Loft in Westbrook

5.0 out of 5 average rating, 58 reviews

Lovely one bedroom studio with on-site parking.

May 16 – 23

ﺩ.ﺇ526 per night
Guest favorite

Loft in Deep River

5.0 out of 5 average rating, 14 reviews

Tree Tops at Lobb Hollow, Carriage House Loft

May 15 – 22

ﺩ.ﺇ843 per night
Guest favorite

Loft in Chester

4.99 out of 5 average rating, 82 reviews

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Apr 25 – May 2

ﺩ.ﺇ658 per night
Guest favorite

Guest suite in Chester

4.92 out of 5 average rating, 65 reviews

Colonial Parmelee House at Guest House Retreat

Nov 22 – 29

ﺩ.ﺇ536 per night
Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 35 reviews

Cozy Loft Getaway

May 10 – 17

ﺩ.ﺇ581 per night
Guest favorite

Home in Haddam

5.0 out of 5 average rating, 69 reviews

Cozy Comforts!

Jun 28 – Jul 5

ﺩ.ﺇ545 per night
Guest favorite

Home in Old Saybrook

4.98 out of 5 average rating, 47 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Feb 14 – 21

ﺩ.ﺇ554 per night
Guest favorite

Home in Essex

5.0 out of 5 average rating, 49 reviews

4-Bedroom Farmhouse *Comfort and Privacy*

Jun 29 – Jul 6

ﺩ.ﺇ2,504 per night
Guest favorite

Home in Essex

4.97 out of 5 average rating, 33 reviews

Ideal Historic Home in Essex Village

Mar 19 – 26

ﺩ.ﺇ1,667 per night
Guest favorite

Home in Chester

4.98 out of 5 average rating, 50 reviews

Tuscan Villa in Chester

Sep 19 – 26

ﺩ.ﺇ2,166 per night

Destinations to explore