Home Vacation Rentals By Owner In Guilford, CT

Showing 20 Of 27 Vacation Rentals
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Exceptional(17)

$280.6

/ Nightly
Private Vacation Home

Cozy Coastal Getaway

Guilford, Connecticut, United States

Welcome to your perfect getaway! Nestled in a picturesque coastal town in CT, this newly renovated gem offers a cozy and comfortable retreat with all the modern amenities you need for a memorable stay. Minutes away from sandy beaches where you can soak up the sun or take a leisurely stroll along the shore. The town is known for its dining options, with a variety of restaurants serving everything from fresh seafood to cozy bistros. Enjoy charming boutiques, apple picking & local farmers markets.brbrThe space:brbrStep into a beautifully updated home featuring stylish decor, plush furnishings, and a welcoming atmosphere. The open-concept living area is perfect for relaxing after a day of exploring. Enjoy the beautiful lit backyard/patio for some relaxation or an outdoor dining experience, or unwind with your favorite shows on the flatscreen TV. The well equipped kitchen is ready for any culinary adventure, and the dining area is ideal for enjoying meals together.brbrThe house offers a comfortable bedroom with a king bed, premium linens and ample storage along with a queen sized air mattress. The newly updated bathroom includes modern fixtures and a refreshing shower.brbrJust a couple minute walk downtown and a few minute bike to the beach!brbrGuest access:brbrGuests have full access to the entire home, including the cozy living area, fully equipped kitchen, bedroom, screened in porch and the private yard & patio. We provide easy self-check-in with a secure key box, so you can arrive at your convenience.brbrOther things to note:brbrThis home not just a place to stay, but a cozy base for your coastal adventure. Whether you’re here to relax on the beach, explore charming local shops, savor delicious meals, or enjoy seasonal activities, you’ll find everything you need right at your fingertips.brbrBook your stay today and experience the perfect blend of comfort, convenience, and coastal charm!
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Sleep 3

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Exceptional(10)

$814.4

/ Nightly
Private Vacation Home

Rivers Edge Unique Newly Renovated River Spa Free-Standing Air Jet Tub retreat

Guilford, Connecticut, United States

Kick back and relax at Rivers Edge, a River Front getaway.brThis spacious newly renovated home was speciacally designed with guests comfort in mind.brbrIdeal for both familes and adult groups, with a large open great room that will easily accommodate everyone. Four Bedrooms with comfortable mattresses and high-end bedding, 2.5 baths. brbrA private woodland park inspired yard leads you to the river, where everyone is sure to gather and enjoy the firepit.brbrThe Space: brGreat Room (Open Concept) brLiving Room has a propane fireplace, 2 full size sofas and a 55 LG smart tv.brDining area has a counter height farmhouse table that can easily accommodate 8 or 10 if you really like your neighbor.brKitchen is fully equipped with everything to cook a gourmet meal (or take out). There is a expansive island with seating for 5 for everyone to critique your cooking skills.brbrBedrooms and baths: You will find 4 bedrooms with comfortable mattresses and high-end bedding. brbrThe primary bedroom has a king size romantic farmhouse wrought iron bed. The en-suite bath features a high-end Bain Ultra Hydro - Thermo Massage free standing tub which features a heated back rest and heated water circulation pump, so the water remains at a constant comfort temperature. A large custom walk in shower and a double sink vanity completes this luxurious en-suite bath.brbrBedroom #2 has a king bed and a 1/2 bath en-suite.brbrBedroom #3 has a queen bed.brbrBedroom #4 has a queen bed. brbrHall bath has a walk-in shower.brbrThere is a pillow selection available, extra blanket and towels.brbrOutdoor spacebrThere is a large deck with a dining table that seats 8, overlooking the river, with a Weber grill for all the grill masters.brA propane fire pit is near the deck or walk down to the river front park area, where there is a picnic table and a wood fire pit for your use.brbrWith advance notice we will be happy to provide a crib or mini crib, pack and play, high chair and baby bath tub.brbrThere are two exterior stairs to access house, once inside house there are 5 stairs to access the complete 2nd floor (main level on bi-level house). brbrGuest Access:brYou will have complete access to the 2nd floor (main level on bi-level house).brOn occassion, lower level maybe rented to a traveling nurse/physician. During these times only outdoor space will be shared (this would be riverfront and fire ring area, all other areas are exclusively yours to enjoy). All entrances are separate and private for that particular unit. brbrAdditional House RulesbrCheck In- 4pmbrCheck Out 10ambrThese times may be flexable with advance notice.brbrHOUSE RULES - RIVERS EDGEbrPrior to BookingbrAll Primary Booking guests MUST read, understand and accept house rules PRIOR to booking and message me back that You have read, understand and accept house rules prior to us accepting reservation.br- Primary Guest booking MUST be at least 25 years old and stay on property entire reservation. Primary Booking Guest must me fully registered, verified with VRBO. Primary Guest must provide there full legal name to book. Maximum Stay is limited to 14 days. No 3rd party bookings allowed. All guests must be registered prior to check in. Primary guest must have 2 positive reviews to book. No gathering allowed other than registered guests. brbrbrHouse RulesbrFor Guest Safety-brPlease do not disable or tamperwith smoke / CO detectors.brbrNo smoking, vaping, e-cigarettes, candles, or fires inside house or on property. A small contained fire is permissable in the fire pit only by the river. We have been on a high drought alert in Connecticut since summer of 2024. Please message us prior to use of fire pit or camp fire due to fire mashshal restrictions.brbrFor safety please only use outdoor dinnerware and plastic wine glasses and cups. They are provided in kitchen area for our guests.brbrWe understand accidents happen, please report any breakage or damage before check out so we may repair or replace for our next guests.brbrOutdoor Music is fine, please keep it low enough not to disturb neighbors. Music/noise must be minimal by 9pm weeknights and 10pm on weekends.brbrPlease remove shoes upon entering house. No rearranging of furniture.brbrWhile we love animals, no pets are allowed due to allergies of future guests. If a guest chooses to disregard policy, we will terminate reservation immediately without refund. Primary booking guest will be charged a mandatory $500 deep cleaning fee. Any damages will be charged to primary booking guest. brbrOf course we welcome ADA certified animals, however we do request if possible please refrain allowing them on bedding or furniture (or cover). Ada animals must be with there owner 100% of the stay. Animals must be cleaned up after. Disturbance or barking to neighbors or others in house will result in termination of the remaining reservation without refund. Primary booking guest is respnsible fr any damages. brbrThank you for your consideration and taking care of our property.brbrCheck out-brPlace rubbish in outdoor bins.brLoad dishwasher, no need to run, we will run cycle.brPlace towels on bathroom floor.brbrThank you for staying with us.brHope you had a great time!! brSafe travels home.
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Bath 2

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Sleep 8

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Exceptional(43)

$742.08

/ Nightly
Private Vacation Home

TREETOPS! A Reunion/Retreat/Event estate! JULY OPENINGS Seasonal POOL! Sleeps 12

Guilford, Connecticut, United States

TREETOPS is a 4850 square ft 5 bedroom Mid century Modern perched on an outcropping of granite cliffs, surrounded by 2 acres of beautiful forest. Perfect for retreats, events, and reunions! brPLEASE NOTE: *Property not suitable for children under 8 years old. 2 small dogs allowed with prior discussion and fee of 50 per night. Events to be discussed prior to booking and there is a reasonable event fee. Nightly rate for 6 guests, additional guests pay 60 a night. Please list all guests upon booking* brbrTreetops is perfect for family reunions, work retreats, rest and relax retreats, yoga retreats, writers' workshops, and even small weddings! Spa services right in town, 5 minutes away. Stroll along the loop trail in our backyard woods, hike in acres of beautiful Westwoods next door, visit the town green with lovely shops, swim at Jacobs beach, have s'mores by the natural stone fire pit, or relax and get some sun by the marine-blue, stone decked pool area with flower garden! Birdwatching, breakfast, yoga, and evening cocktails are best on the spacious wrap-around deck. We also have an incredible library, fireplaces, and even a baby grand piano! brbrThe spacebrThe inside of Treetops is spectacular, where classic and modern styles blend. Antiques are plentiful but so too are modern paintings, sculptures, and other unique art. Our love of indigenous cultures will be obvious, and we don't shy away from colors as well! Beautiful, lush plants give the house a welcoming, homey feel.brbrTreetops has vaulted ceilings, and an open and spacious floor plan. There is a great kitchen with new appliances, a two-person breakfast nook, and an oversized dining area and living room overlooking the oversized deck mentioned above. Perfect for social gatherings of all kinds! Plentiful windows and slider doors flood the house in sunlight and fresh breezes. brbrThe large living room has a top-of-the-line stereo system, CDs, large Smart TV, impressive fieldstone fireplace, and extensive library. Grab a book and recline on the new sofa while listening to some classical music! From there, walk into the master bedroom with more windows and wooded views, TV with DVD player and huge selection of movies, walk-out deck, and walk-in closet. The tiled bathroom has two sinks, a jetted tub for easing sore muscles, and a great shower/showerhead, with some basic amenities available for your stay. brThen walk into the Blue room, a bedroom with 1 Twin bed and 1 Full bed overlooking the driveway with bureau, bedside table, and bookshelves. Guests in this room will share the master bathroom for bathing but can also use the half bathroom near the front entrance. brbrA hallway then leads to the newly appointed den, with new TV, sofas, and a second beautiful fieldstone fireplace. There are games and coloring books available in the cabinet. brbrAcross from the den and off the main entrance is the Yellow room. It too is newly renovated and has a Full bed, large built-in desk overlooking the pool, views galore, and a cozy reading nook that can also double as a second place to sleep.brbrUpstairs are two bedrooms, The Queen, with a queen-size bed, and The Twins with -- you guessed it -- 2 twin beds. Both rooms have bureaus, bedside tables, one or two oversized windows, sound machines, fans, and their own full bathroom. You are really in the treetops up here! Enjoy your stay.brbrOther things to notebrNightly rate is for 6 guests. additional guests are 60 dollars a night.brbrWe are near some railroad tracks and a few times a day, mostly morning and evening, trains go by. You will definitely hear them if you are awake, but we have never been bothered by them when sleeping.brbrThe Pool is scheduled to be available between Memorial Day and Labor Day weather permitting.brbrSee house rules for additional information.brbrIf we can be of help during your stay, please contact us. Please reach out with any questions! Thanks for choosing Treetops.
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Bath 2

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Sleep 12

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Exceptional(32)

$598.0

/ Nightly
Cottage

1930s Waterfront Cottage on Tuttle's Point

Guilford, Connecticut, United States

Remember 'doing the dishes' with family members and friends Do you love an outdoor shower Visit this charming 1930's summer cottage with direct water access, large screened porch with wonderful 180 degree views of Long Island Sound. Little White Top is unpretentious and comfortable, designed to allow for carefree and peaceful holidays.brbrThe long and airy screened porch overlooking the water is the hub of the home, where everyone wants to gather to read and converse, sharing breakfast, lunch, or cocktails. And it's a wonderful place to watch a thunderstorm! The cottage comfortably sleeps 6 people, with 2 bedrooms on the first floor with queen beds, and 3 bedrooms on the second floor, one with a queen bed, one with a double bed, and the third with a double bed and 2 twin beds. There is ample parking on the property for 4 cars.brbrMoor your own boat in the waters off the shore. Easy launching of kayaks and canoes can be done directly from the property and from the beach just down and around the corner. Kids can choose to paddle around the protected waters off Tuttles Point or go out to the various rock islands and explore the tide pools there. More adventurous adults can embark on longer paddles to Faulkner's Island Island Light or to Sachem's Head or the Thimble Islands. Enjoy picnics on the front lawn, with ample space for children to play. Sun yourselves and take a dip at the water's edge or take the little ones 600 feet down the hill to the sandy Association Beach. brbrThe protected waters off Tuttles Point offer swimming, fishing, and kayaking and their protected nature is especially good for children. At all tides, ospreys, herons, gulls, and other shorebirds seek out these waters and the rich marshlands nearby.brbrYou may notice in the listing there is no TV! Little White Top is the kind of place where you can step aside from your usual routine, listen to one another and the coastal sounds. You are in a different place and there is a strong tradition of Monopoly and Scrabble here!brbrTuttles Point is a quiet, low-key residential neighborhood in a private association with its own beach, in the historic town of Guilford. Guilford Town Center offers interesting shopping and fine dining, Shakespeare on the Green in August, as well as craft and antique shows. A Pick-Your-Own farm/orchard is an 8 minute drive from the Cottage. Collect some berries and bake a pie in the simple but well appointed kitchen! Biking and hiking trails are easily accessible, as well as the local Whitfield House Museum. The Peabody Natural History Museum and the British Art Museum at Yale University are a 1/2 hour drive to be enjoyed along with Frank Pepe's Pizza in New Haven, considered to be the very best! Rentals are from Friday to Friday. Arrivals or departures outside of this standard may be possible. Please inquire with host. We look forward to welcoming you to this very special spot!
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Sleep 8

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Exceptional(1)

$445.21

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Private Vacation Home

Artistic Modern Forest Retreat minutes from Guilford town center and shores

Guilford, Connecticut, United States

Modern Home in the Trees | 5 Min to Beach & Guilford GreenbrbrThoughtfully designed on a stone slope, this modern home welcomes you on the top floor, where you descend into a soaring, light-filled space surrounded by forest. A deck overlooks a private trail through three secluded acres, yet you’re just minutes from historic Guilford Green and beaches. Artist-owned, the home features thoughtfully curated furnishings and artwork that enrich its distinctive design. brbrPerfect for couples or long-term summer guests seeking tranquility, nature, and artistic charm.brbrPlease note: we host longer stays only — one to two months.brbrThe Spacebrbr• Two bedrooms, each with a king bedbr• Two full bathrooms with shower/tub combosbr• Floor-to-ceiling windows with immersive forest viewsbr• Private deck with grillbr• Picnic table set among the treesbr• Original artwork and designer furnishings throughoutbr• Complete privacy, minutes from townbr• Beach pass includedbrbrThe SettingbrbrGuilford is one of Connecticut's most beloved shoreline towns — historic, walkable, and quietly sophisticated.brbr• 5 minutes to the Guilford Green, one of New England's largest and most picturesque town greens, lined with 17th-century buildings, shops, galleries, and restaurantsbr• 5 minutes to Connecticut shoreline beachesbr• Bishop's Orchards (since 1871) for pick-your-own fruit, produce, and local winebr• Short walk to the Westwood Hiking Trails entrancesbr• Short drive to Guilford's Jacob Beach and Chaffinch Island Parkbr• Easy drive to Madison and Hammonasset Beach State Park
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Sleep 5

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Exceptional(18)

$308.28

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Cottage

Guilford Carriage House at Granite Lodge!

Guilford, Connecticut, United States

Escape to this Guilford vacation rental situated on 4.5 acres equipped with a laptop-friendly workspace and free WiFi! This 1-bedroom, 1-bath cottage with a loft boasts a newly updated interior with stainless steel appliances, luxe vinyl floors, 2 Smart TVs, and a charming bathroom featuring a clawfoot bathtub. Spend your stay strolling Jacobs Beach, visiting a nearby winery and orchard, exploring historic Yale University and downtown New Haven, and swimming in the shared, on-site seasonal pool!brbr-- THE PROPERTY --brbrFree WiFi | Laptop-Friendly Workspace | In-Unit Washer + Dryer | Fire Pit | Central Air ConditioningbrbrBedroom: King Bed | Loft: 2 Twin BedsbrbrOUTDOOR LIVING: Boating, near marina/ocean, vernal pool, outdoor seating w/ umbrella, shared seasonal pool (open Memorial Day-Labor Day between 10:00 AM-6:00 PM)brINDOOR LIVING: 2 Smart TVs w/ cable + streaming, clawfoot bathtub, shower, walk-in closet, board gamesbrKITCHEN: Refrigerator, wood-burning stove (decorative only), oven, dishwasher, coffee maker, coffee grinder, blender, water filter, cooking basics, dishware/flatwarebrGENERAL: Ceiling fans, central heating, linens/towels, complimentary toiletries, hair dryer, hangers, iron/board, laundry detergent, trash bags/paper towelsbrFAQ: Step-free access via side door, 3 external surveillance cameras (facing outward), quiet hours (11:00 PM-8:00 AM)brPARKING: Driveway (2 vehicles), 4WD recommended in winterbrbr-- THE LOCATION --brbrGET OUTSIDE: Westwoods Hiking Area (0.5 miles), Jacobs Beach (6 miles), Stony Creek Beach (6 miles), Timberlands Hiking Area (10 miles), Hammonasset Beach State Park (13 miles)brNEARBY ATTRACTIONS: Bishop’s Orchards Farm Market & Winery (3 miles), The Woodwinds - event venue (4 miles), Rose Vineyards (4 miles), Guilford Center (4 miles), The Guilford Fair & Fairgrounds (5 miles), Stony Creek Museum (5 miles)brNEW HAVEN: Yale University (13 miles), Long Wharf Park (13 miles), Downtown New Haven (14 miles), Westville Music Bowl (15 miles), New Haven Country Club (16 miles)brAIRPORT: Tweed New Haven Airport (11 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The seasonal pool is shared with Granite Lodge and is open Memorial Day - Labor Daybr- NOTE: 4-wheel drive or all-wheel drive is necessary in the winter months to access the propertybr- NOTE: The wood-burning stove is decorative and is not available for guest use br- NOTE: Your safety matters. This property features 3 exterior security cameras. Camera 1 is located on the front exterior of the cottage facing outward toward the driveway, camera 2 is located at the shared pool area facing the pool, and camera 3 is a Ring doorbell camera located at the front door entry. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion. They will record when they first sense motion and 30 seconds after the last motion is detectedbr- NOTE: Please observe quiet hours between 11:00 PM-8:00 AMbr- NOTE: The loft is accessible via a ladder. The ladder is for use at your own risk
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Exceptional(19)

$278.3

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Private Vacation Home

Welcoming Tiny Home! Downtown & Beachy☀️

Guilford, Connecticut, United States

Seagrass Bungalow is a sun filled, romantic, peaceful, back to nature, mini-home, that is exactly where you are meant to be! Private & surrounded by seagrass blowing in the breeze & cheerful birds waking you with the sunrise. Seagrass Bungalow is the perfect getaway for two & their small pup. Do yoga on the private deck, shower outdoors in the sunlight, grill local corn, have a cocktail by the firepit, or get out & walk to the cutest town green, shops, restaurants, & beach! ☀️brThe spacebr Seagrass Bungalow is a very cool…Modern, beachy, boho flare, that just feels awesome to be in. Super cozy inside & back-to-nature outside. Great spot to unplug, sunbathe, listen to birds, bathe in the outdoor hot/cold shower, meditate on the deck, toast with cocktails, grill, stargaze while lounging at the fire pit. Time for a little more excitement !Stroll with your pup for a short walk to idyllic downtown Guilford. Lots of really good restaurants from breakfast crepes & scones to farm-to-table dinners at night. Catch local bands & weekend entertainment on the town green. Get a little more exercise and take a run down to our local Jacobs Beach & watch the sunset.☀️brGuest accessbr Seagrass Bungalow is a brand new, private mini-home. It shares a beachy, marsh-front property with the owners charming cottage. Guest entrance is separate & Seagrass Bungalow is situated with plant-filled fencing for the utmost privacy. Seagrass Bungalow guest area includes the entire bungalow inside, the outdoor deck, & stone patio areas within the private fencing. Larger grass yard & cottage outside of fencing is owners’ space with their small dog. Seagrass Bungalow has one designated parking space but others can be available easily.☀️brbrHouse rulesbrYou'll be staying in someone's home, so please treat it with care and respect.brChecking in and outbrCheck-in after 1:00PMbrCheckout before 10:00 AMbrDuring your staybr2 guests maximumbrPets allowedbrCommercial photography allowedbrAdditional rulesbrWe love dogs at Seagrass Bungalow . We have our own small dog on the property. Arlo!! He runs a little free but is very shy and sticks close to us. He loves other dogs but does not have access to your fenced in area! Please keep your cute doggie on a leash when leaving Bungalow .brBefore you leavebrTurn things offbrReturn keys & beach pass
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