Romantic Guesthouse in Historic Downtown Waterfront District!

Mystic, Connecticut
$260 avg/night
Minimum Stay 2 Nights
Bed 1

Bed

Bath 1

Bath

Home Guest House

Property Type

Sleep 2

Max Sleeps

Night 2 nights

Min Stay

Let the Cliffside Guesthouse become your gateway to the fun, excitement and relaxed New England charm of historic southeastern Connecticut. Cast off the burdens of daily life and journey to Mystic, a historically avant-garde seaport community that combines the best of both yesterday and today. Located just steps from the Mystic River, and situated only blocks from the center of this little hamlet, the Cliffside Guesthouse provides you with easy access to award-winning restaurants, world class casinos, unique shops, historic museums, and exciting attractions.

Recently constructed in June, 2017, and now new to the rental marketplace, the Cliffside Guesthouse is furnished to suit all of your vacation needs. Accommodations include a comfortable sitting area with TV and internet connections and a fully-functional kitchen with electric stove and oven, refrigerator, microwave, toaster, coffee machine, cookware, plates, and utensils. The guesthouse also includes a beautiful separate bedroom overlooking our beautiful cliff, and a spacious bathroom including a full-sized, glass-enclosed, step-in shower and vanity. The guesthouse is centrally air-conditioned with separate controls for the living space and bedroom areas. Best of all, you will be able to open the sliding glass doors to access your own personal veranda, overlooking the town’s historic district and surrounding neighborhood gardens.
The Cliffside Guesthouse is less than two hours from Boston and New York, and only a short drive from anywhere in Connecticut. A quick walk from the train station and you will find a unique place to unwind and rediscover the pleasures of life in comfort. In Mystic, you can eat lobster at seaside lobster shacks while watching boats embark upon their world-wide destinations, play games of chance at renowned casinos, or even enjoy intimate moments along our riverside boardwalk. The famous Mystic Pizza, along with many other award-winning restaurants, is only a 10 minute walk away, and the Mystic Seaport and Mystic Aquarium are readily accessible. Or walk or bike along River Road, Connecticut’s first designated Scenic Roadway. Watch Hill, Westerly, Misquamicut Beach, and Newport, Rhode Island are all only a short drive away.

Accommodations include walking distance to downtown Mystic and private on-site parking. A pleasant 15 minute drive through the back roads of rural Connecticut will find you enjoying the contemporary excitement of Foxwoods and Mohegan Sun casinos. Holiday and Special Occasion Gift baskets are also available upon request. Our personal attention in preparing for your holiday experience may include specialty breakfasts, wedding and event services, spa experiences, charter fishing and boat cruises, and wine tours, or we will be happy to design one of your own choice. Arrangements for local sightseeing tours and local restaurant selections are also available for those without transportation. This property is available for Winter and long-term rentals.

We look forward to seeing and serving you soon at the Cliffside Guesthouse!


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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • MORE

    Beach Towels Books Games Smoke-free Property Iron/ironing Board
  • OUTDOOR

    Beach Loungers Garden Outdoor Furniture
  • PARKING

    Onsite Parking Includes Off-street Options
  • INTERNET

    Available In All Rooms: Free WiFi Available In Some Public Areas: Internet Access In-room WiFi Speed: 250+ Mbps (good For 3–5 People Or Up To 10 Devices)
  • LANGS SPOKEN

    English
  • FAMILY FRIENDLY

    Dining Table Kitchen Microwave Refrigerator
  • ACTIVITIES NEARBY

    Birdwatching Casino Cycling Ecotours Fishing Fitness Center Access Golfing Health/beauty Spa Hiking/biking Trails Horse Riding Hunting Ice Skating Jet Skiing Kayaking Marina Motor Boating Mountain Biking Outlet Shopping Sailing Scuba Diving Swimming Water Skiing Water Tubing Whale Watching Wildlife And Game Walks Winery Tours
  • BEDROOM

    Air Conditioning Bed Sheets Heating
  • BATHROOM

    Hair Dryer Shower Soap Toilet Paper Towels
  • ENTERTAINMENT

    Cable/satellite Channels Smart TV
  • OUTDOOR SPACE

    Balcony
  • FOOD AND DRINK

    Blender Coffee/tea Maker Cookware/dishes/utensils Dining Table Electric Kettle Kitchen Lobster/crab Pot Local Meal Delivery Service Microwave Oven Paper Towels Refrigerator Stovetop Toaster

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 2

Map Map

School District Availability

Review Review

  • Dane

    Submitted Apr 12, 2025

    Stayed Apr 10, 2025

    The host of this property is amazing! We felt so welcomed and relaxed the entire stay. The vibe is cozy and made us feel right at home we didn't want to leave!! Highly recommend and we will absolutely be back!

  • Diana

    Submitted Nov 2, 2024

    Stayed Oct 30, 2024

    Charming space above garage with lots of privacy. Very nicely appointed. Walk to stores and restaurants.

  • Henry

    Submitted Oct 28, 2024

    Stayed Oct 25, 2024

    We could not have asked for a better experience! Anne was extremely hospitable and friendly. Would definitely recommend!

  • Melissa

    Submitted Jun 6, 2024

    Stayed May 22, 2024

    It was so close to town. You walked through a truly historic neighborhood which was both beautiful and quiet. Our hosts were so friendly, informative and truly hospitable,it was like staying at a friend’s house. Your space is separate from the main house so it was very private. I highly recommend this place. We hope to return.

  • David

    Submitted Feb 21, 2023

    Stayed Feb 17, 2023

    Really nice place to stay in Mystic. Comfortable, spacious and easy walk to town. Hosts are wonderful.

  • K

    Submitted Oct 30, 2019

    Stayed Oct 25, 2019

    This is a lovely property in a safe, historic neighborhood within walking distance of downtown Mystic and its shops and restaurants. It is very private - you really have your own little apartment. Everything looked clean and brand new. I was travelling alone for work and felt totally safe and comfortable here.

  • Submitted Jul 11, 2019

    Stayed Jul 4, 2019

    Cozy, clean, well set up. Walking distance to town. Quiet and pretty.

  • Joyce H.

    Submitted Jun 12, 2026

    Stayed Jun 10, 2026

    Such a perfect, peaceful place to stay and enjoy Mystic! Annie is a wonderful hostess!

  • Mike S.

    Submitted May 30, 2026

    Stayed May 18, 2026

    Very clean, comfortable property. Great location. Quiet but a short and easy walk to downtown.

  • Kent B.

    Submitted May 27, 2026

    Stayed May 21, 2026

    This is a really nice property in a quiet neighborhood with a short walk to Mystic shops, restaurants and seaport.

  • April D.

    Submitted May 26, 2026

    Stayed May 16, 2026

    Anne was an absolute wonderful host and the property could not have been more beautiful. We loved the special touches and we had an amazing weekend. We will be back again next year and look forward to many stays ahead.

  • kathryn g.

    Submitted May 11, 2026

    Stayed Apr 27, 2026

    Nice kitchen and extremely safe parking

  • Nancy B.

    Submitted Apr 20, 2026

    Stayed Apr 14, 2026

    We had a wonderful stay at The Guesthouse. The location is ideal for walking to Mystic’s shops & restaurants, yet tucked away enough to feel peaceful and relaxing. The hosts are fantastic and shared great tips. Highly recommend!

  • Dorothy L.

    Submitted Apr 11, 2026

    Stayed Mar 31, 2026

    We had a relaxing, comfortable stay at the cottage! After a full day of wandering and exploring sites in Mystic and beyond it was lovely to come “home” to reinvigorate before dinner. The host was so lovely and the cottage was well appointed with every necessity and convenience. We would go back in a heartbeat!

  • Jeffrey O.

    Submitted Mar 8, 2026

    Stayed Mar 6, 2026

    Excellent host and great stay!

  • Matthew H.

    Submitted Mar 1, 2026

    Stayed Feb 27, 2026

    Host was great. Met us at check in and spoke to us when we departed.

  • John B.

    Submitted Feb 24, 2026

    Stayed Feb 19, 2026

    Ann was an awesome host. Recommend this place especially with the location. When it’s warmer, you can walk to practically everything.

  • E. R.

    Submitted Jan 19, 2026

    Stayed Jan 15, 2026

    What a quaint and cozy place to stay. The host was amazing and the central location in Mystic made it a great base. Highly recommend!

  • James B.

    Submitted Dec 7, 2025

    Stayed Dec 5, 2025

    Beautiful property in a perfect location!

  • Landon F.

    Submitted Oct 29, 2025

    Stayed Oct 26, 2025

    We loved this location! Everything was so easy and beautiful. Would definitely stay here again.

  • Vicki G.

    Submitted Oct 24, 2025

    Stayed Sep 15, 2025

    Be aware that the rental unit is over the garage in the back of the picture. But do not hesitate to stay at this location. It was delightful. Thoughtfully furnished, great kitchen and bathroom. Easy walk to all the town of Mystic has to offer. The host was gracious, welcoming and helpful. I would return unhesitatingly.

  • Gaye R.

    Submitted Oct 8, 2025

    Stayed Oct 5, 2025

    The property is just 2 blocks from downtown which is important as parking is expensive and limited. The host is wonderful and we enjoyed the cozy and quiet property and would stay again when we visit Mystic.

  • Harvey B G.

    Submitted Oct 7, 2025

    Stayed Oct 2, 2025

    The host was fantastic and made us feel at home. She stayed up till we got it at 3 am. The space is a perfect size, and very comfortable. Everything was in walking distance, which is exactly what we wanted. Definitely will return.

  • Carol G.

    Submitted Sep 20, 2025

    Stayed Sep 18, 2025

    Great location and beautifully kept property.

  • Ken H.

    Submitted Sep 10, 2025

    Stayed Aug 29, 2025

    Great stay - very cute and comfortable place in great location. Host was very nice and helpful!

  • Shelley B.

    Submitted Aug 17, 2025

    Stayed Aug 9, 2025

    Lovely apartment in a beautiful setting. Super easy check-in. She came out to meet us when we drove in.

  • C. A. F.

    Submitted Aug 15, 2025

    Stayed Aug 2, 2025

    Wonderful vacation in the town of Mystic! Comfortable, clean & yes - romantic!

  • Joanne L.

    Submitted Jun 29, 2025

    Stayed Jun 27, 2025

    Wonderful guesthouse. Perfect for my husband and myself. Super clean, easy parking, and fabulous location.

  • Alice T.

    Submitted Jun 27, 2025

    Stayed Jun 24, 2025

    Ann, is a very gracious host. We’ve stayed at the guest house before and enjoyed it immensely and were happy to find it available for our time period. The location can’t be beat! You can walk to Main Street to shop, to dine and to just enjoy the Mystic River. You park the car and that’s it!We’ll be returning.Alice T.

  • Susan C.

    Submitted Jun 23, 2025

    Stayed Jun 13, 2025

    Cute spot that is on a quiet street yet an easy walk into the village. More charm than staying at a hotel and has all the conveniences of a kitchen. But know that the ambiance is more on the antique side and we've let the owner know that the linens could use a refresh.

  • Dorothy O.

    Submitted Jun 23, 2025

    Stayed Jun 20, 2025

    I recently stayed at Cliffside Guest House in Mystic because I was in town two family parties--a wedding and a going away party. The guesthouse was a perfect choice. Everything is as described online and there are cute extra touches, such as reader glasses just in case! The place was immaculate and comfortable. The owner, who lives on site, was available yet not intrusive at all. The location is within easy walking distance to shops and restaurants and only a short drive to the RI beaches. I would love to stay again and recommend this spot for anyone wanting to explore the area.

  • Amanda J M.

    Submitted Jun 9, 2025

    Stayed Jun 6, 2025

    Perfect place to stay you can walk to mystic downtown area and short drive to stonington borough. Quiet neighborhood.

  • elizabeth d.

    Submitted Jun 6, 2025

    Stayed Jun 4, 2025

    This VRBO is the perfect getaway

  • Bryant E.

    Submitted Jun 2, 2025

    Stayed May 21, 2025

    This property is conveniently located in a quiet neighborhood, an easy walk to the shops and restaurants in downtown Mystic. It provides privacy, given that it is above the garage and detached from the owner's home. It is bright and cheerful, immaculate, and comfortably furnished. Everything was in working order. We enjoyed our stay.

  • Terry N.

    Submitted May 15, 2025

    Stayed May 11, 2025

    The property was nicely decorated and well stocked, and, the host was very friendly and helpful. One of the things we liked best was the short walk to town with shopping and restaurants. If we would return to the area, we would stay here again!

  • Don G.

    Submitted Apr 25, 2025

    Stayed Apr 18, 2025

    Oh my! 5 out of 5 stars? NO! 10 out of 5 stars! This location is not only the place to stay when visiting Mystic, but is in fact a reason to visit Mystic. Anne (as in Oakley) is the consummate host. Greeting us upon arrival and providing us with a person tour of her beautiful property. And beautiful it is! The rental unit is on the second floor above a garage. (Please note the presence of steps.) Everything is so clean it is as if it were new. Beautiful and tasteful decorating. Comfortable queen bed. Nicely equipped kitchen and spacious living quarters. AND, walking distance to quaint Mystic main street. During our 1.5 week road trip Anne's place was hands down our favorite location. I cannot recommend this rental highly enough. Love it.

  • Lynn M.

    Submitted Apr 17, 2025

    Stayed Apr 15, 2025

    This property is Beautifully decorated, nicely stocked, newly built 8 years ago. Perfect getaway location.

  • Christine S.

    Submitted Apr 13, 2025

    Stayed Apr 7, 2025

    Could not imagine in Mystic that there is a more convenient location to town with a beautiful view and a well-designed and cared for cottage as the one that Anne Esposito owns and rents. We had a very enjoyable time, and the cottage environment is quiet and very comfortable bed and well stocked kitchen. Thank you, Anne, you'll see us again!

  • Kimberley S.

    Submitted Mar 29, 2025

    Stayed Mar 26, 2025

    Anne‘s place is clean, cozy, and convenient. She has provided everything you could possibly need for an idyllic stay in Mystic. The house is easy walking distance to the downtown area, the perfect location for exploration. I just can’t say enough about this lovely rental and Anne was the perfect hostess, giving me tons of helpful, information tomake the most of my stay.

  • Heather T.

    Submitted Mar 17, 2025

    Stayed Feb 28, 2025

    Property was beautiful, location perfect. The owner felt the need to call me repeatedly before my stay and then we had to do a meet n greet which seemed uneccesary. She had to give us a tour etc... there was a very detailed binder explaining all the details of the Property. Overall very nice stay.

  • Traci L.

    Submitted Feb 18, 2025

    Stayed Feb 7, 2025

    What a lovely stay! Location is convenient to down town. Large bathroom, clean and comfy sitting/TV area, everything you need to cook and a comfy bedroom! We loves our stay and cant wait to come again!

  • Heidi T.

    Submitted Feb 2, 2025

    Stayed Jan 31, 2025

    So cozy, like home. Easy walking to downtown! The owners are wonderful!

  • Stephanie S.

    Submitted Dec 31, 2024

    Stayed Dec 27, 2024

    We had a wonderful stay at the Cliff Guesthouse. The house has a well equipped kitchen, large shower, comfortable living room and bedroom. The location is great for exploring Mystic. We were able to catch up on some well deserved rest and relaxation after the holidays. I would highly recommend staying here if you are visiting the area.

  • Tyler G.

    Submitted Dec 11, 2024

    Stayed Dec 6, 2024

    Excellent cozy space! Great location, can walk to downtown Mystic. Very nice interactions with host!

  • Robin H.

    Submitted Oct 15, 2024

    Stayed Oct 11, 2024

    I found the Cliffside Guesthouse to be lovely inside and out. It is in a very quiet and peaceful location. It is clean, comfortable and very well kept. The host was very responsive and I would definitely stay here again. The host, Anne, met me when I first arrived and explained all the things relative to the workings of the usual appliances, as well as the AC/heat, parking, etc. She really made me feel comfortable and made herself available for any questions. There was coffee for the first morning, which was very much appreciated and an extra bonus is the parking is on property! Also, I was grateful for the extended check-out time. The Guesthouse is in such a great part of Mystic making it a quick walk (10-15 mins) to the center of Mystic with its restaurants, shops, and, my favorite, the Mystic Bascule bridge. It just a short drive (6-8 mins) to the Mystic Seaport Museum. On my very first morning I opened the door to the little balcony and sat at the dining table with my coffee and did some very easy birdwatching as the birds sang and flitted in and out of a nearby tree. It would have been nice if I had remembered my binoculars! Thank you, for the wonderful stay that made my weekend absolutely perfect!

  • Mike S.

    Submitted Sep 30, 2024

    Stayed Sep 22, 2024

    Over the years we have had numerous stays in Mystic CT but by FAR, the Cliffside Guest House was the absolute best. Sweet one bedroom apartment within walking distance of all the restaurants, shops, attractions, located in the historic district of Mystic. Yes, walking distance and that is HUGE in crowded Mystic. But I have to give a shout out to the owner, Anne. She thought of EVERYTHING to make sure we were comfortable. Adequate storage space, Walk in closet (with hangers), Umbrella's at the ready. Lovely comfortable bed. Beautifully decorated. Anne greeted us at the door, showed us the ropes and was always available (on site!) for questions or recommendations. We have done numerous numerous VRBO's in our travels but Anne and Cliffside Guesthouse is the 100% BEST, no question about it. Thank you Anne (and Ken) for your kind hospitality and vision. We will be back! (we took your card:) )

  • Melissa W.

    Submitted Sep 24, 2024

    Stayed Sep 20, 2024

    The location was beautiful nestled in a small quiet neighborhood yet walking distance to town. The listing was exactly as described… no surprises! The hosts were wonderful and so inviting and helpful! I enjoyed my morning talk with Anne. We would definitely recommend!

  • Joseph M.

    Submitted Sep 16, 2024

    Stayed Sep 13, 2024

    Anne and Ken were wonderful hosts! It was an exceptional accommodation!

Your dates are Available!

Total

Includes taxes and fees
$275+
View details