Guilford holiday rentals

We found 763 holiday rentals — enter your dates for availability
Discover a selection of 29 homes and other holiday rentals in Guilford that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Guilford

Showing deals for:11 Dec - 18 Dec

Interior
Exterior
Room
Living area
Exceptional
(67 reviews)

Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

Westbrook

8% off
AU$9,792
for 7 nights, 1 home
AU$1,399 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Cozy seating area with dual water views
You will love the Center Island cooktop open kitchen & beautiful water views
Sunsets are simply breath taking over the water
Experience Stunning panoramic Water Views from every area of the home
Exceptional
(73 reviews)

Waterfront Retreat, Private Beach + Hot Tub Sunsets

Branford

14% off
AU$14,309
for 7 nights, 1 home
AU$2,044 per night
includes taxes & fees
Waterfront Retreat, Private Beach + Hot Tub Sunsets
Exterior
Exterior
Exterior detail
Beach
Wonderful
(59 reviews)

2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT

Old Lyme

8% off
AU$3,603
for 7 nights, 1 cottage
AU$515 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Side of House with outdoor shower to rinse off from the beach.
Front of House
Aerial view of back deck area
Kitchen
Exceptional
(11 reviews)

4 BED/2 BATH -PRIVATE BEACH: OLD COLONY

Old Lyme

7% off
AU$6,858
for 7 nights, 1 home
AU$980 per night
includes taxes & fees
4 BED/2 BATH -PRIVATE BEACH: OLD COLONY
Welcoming living room for quiet conversations.
The new splash pad will be a hit with the little ones.
The Guilford train station is 1/3rd of a mile away. Need to be in the city?
Special sunsets overlook the harbor and the Lobster Pound.
Exceptional
(32 reviews)

Great home walkable to everything!

Guilford

8% off
AU$6,842
for 7 nights, 1 home
AU$977 per night
includes taxes & fees
Great home walkable to everything!
Interior
Outdoor dining
Property grounds
Dining
Exceptional
(5 reviews)

On the Water Spacious Comfortable Historic Home

West Haven

8% off
AU$9,578
for 7 nights, 1 home
AU$1,368 per night
includes taxes & fees
On the Water Spacious Comfortable Historic Home
Exterior
Living area
Living area
Private kitchen
Exceptional
(16 reviews)

Spacious Modern Beach House, perfect for families

Branford

8% off
AU$6,823
for 7 nights, 1 home
AU$975 per night
includes taxes & fees
Spacious Modern Beach House, perfect for families
Property grounds
Property grounds
Entryway 🐳
Kitchen
Exceptional
(17 reviews)

Cornfield Point Cottage

Old Saybrook

8% off
AU$11,272
for 7 nights, 1 home
AU$1,610 per night
includes taxes & fees
Cornfield Point Cottage
Home from the water. (Blue house in center of photo)
Interior
(new photo 6/25/2011)
master bedroom, king bed.
Exceptional
(53 reviews)

Beautiful Waterfront Beach House for Family Vacations

Branford

8% off
AU$8,498
for 7 nights, 1 home
AU$1,214 per night
includes taxes & fees
Beautiful Waterfront Beach House for Family Vacations
Private kitchen
Interior
Living area
Living area
Excellent
(5 reviews)

Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches

East Haven

7% off
AU$4,165
for 7 nights, 1 home
AU$595 per night
includes taxes & fees
Luxury New Haven Retreat • Private Pool, Gym, Cinema • Near Yale & Beaches
Winter blaze
Winter afternoon from the boathouse
Ipe deck in the morning sun
Full chef's kitchen with new appliances
Exceptional
(6 reviews)

Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet

Old Lyme

16% off
AU$8,420
for 7 nights, 1 home
AU$1,203 per night
includes taxes & fees
Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet
Private kitchen
Dining
Exterior
Pool
Exceptional
(7 reviews)

Private Home - Pool and Close to CT Shoreline Beaches

North Branford

17% off
AU$13,723
for 7 nights, 1 home
AU$1,960 per night
includes taxes & fees
Private Home - Pool and Close to CT Shoreline Beaches
Kitchen
Back deck
Living room, bathed in morning light
Interior
Wonderful
(90 reviews)

Historic New England home ,Reunions Beach pass

Guilford

8% off
AU$4,071
for 7 nights, 1 home
AU$582 per night
includes taxes & fees
Historic New England home ,Reunions Beach pass
The Kitchen
Lake View
Living Room
Living Room
Exceptional
(15 reviews)

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

New Haven

8% off
AU$2,269
for 7 nights, 1 home
AU$324 per night
includes taxes & fees
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Interior
Exterior detail
Living area
Private kitchen
Exceptional
(22 reviews)

Ocean View cottage in Indian Neck. Super Host with 5-Star Rating

Branford

7% off
AU$2,006
for 7 nights, 1 home
AU$287 per night
includes taxes & fees
Ocean View cottage in Indian Neck. Super Host with 5-Star Rating
Interior
Exterior
Beach
Living area
Exceptional
(55 reviews)

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Old Lyme

8% off
AU$2,798
for 7 nights, 1 cottage
AU$400 per night
includes taxes & fees
2Bdr Beachfront; 11B second floor, Old Colony Beach , CT
family room
Beautiful sun room for dining
Newly remodeled kitchen
family room
Exceptional
(27 reviews)

Make Memories in Charming Hawk's Nest Beach!

Old Lyme

8% off
AU$3,594
for 7 nights, 1 home
AU$513 per night
includes taxes & fees
Make Memories in Charming Hawk's Nest Beach!
Room
Beach
Living area
Private kitchen
Exceptional
(32 reviews)

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

Clinton

11% off
AU$4,101
for 7 nights, 1 home
AU$586 per night
includes taxes & fees
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Dining
Terrace/patio
Exterior
Room
Exceptional
(46 reviews)

4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy

East Haven

17% off
AU$6,092
for 7 nights, 1 home
AU$870 per night
includes taxes & fees
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
Queen Bedroom 2
Stairwell to Master
Living Room
Dining Room
Excellent
(6 reviews)

Beach Apartment in Woodmont Milford

Milford

7% off
AU$2,504
for 7 nights, 1 apartment
AU$358 per night
includes taxes & fees
Beach Apartment in Woodmont Milford
Deck
Exterior
Living Room with view of expandable dining table
Loft View of Living Room
Exceptional
(91 reviews)

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton

7% off
AU$2,042
for 7 nights, 1 cottage
AU$292 per night
includes taxes & fees
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Living area
Interior
Interior
Exterior
Wonderful
(30 reviews)

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Branford

8% off
AU$2,988
for 7 nights, 1 home
AU$427 per night
includes taxes & fees
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Chef's kitchen with cooking supplies, large island, and ample cabinet space.
Enter into the open floor plan with updated kitchen, living, and family room.
Seat 6 people at the dining table, or use it to get some work done.
Gateway to tranquility at the private beach is only a 5 minute walk.
Exceptional
(82 reviews)

UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

Westbrook

8% off
AU$4,590
for 7 nights, 1 home
AU$656 per night
includes taxes & fees
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The trendy area of Guilford awaits your stay

Enjoy the wineries and other features of Guilford. This trendy and welcoming city entices travellers with its restaurants and sightseeing. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Guilford

Are you hoping to find things to do during your stay? Venture out of your cosy holiday rental and experience everything that makes Guilford a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Chatfield Hollow State Park (6.9 mi / 11.1 km)
  • Powder Ridge Mountain Park and Resort (15.1 mi / 24.3 km)
  • Machimoodus State Park (17.6 mi / 28.3 km)
  • Brownstone Exploration & Discovery Park (19.8 mi / 31.9 km)
  • TPC River Highlands (23.8 mi / 38.3 km)
  • Mount Southington Ski Area (24.1 mi / 38.7 km)

Exploring the natural features in Guilford

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Guilford is a great place to spend some time outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Chatfield Hollow State Park (6.9 mi / 11.1 km)
  • Hammonasset Beach (7.2 mi / 11.6 km)
  • Clinton Town Beach (8.2 mi / 13.1 km)
  • Double Beach (8.4 mi / 13.6 km)
  • East Haven Town Beach (10.5 mi / 16.9 km)
  • Westbrook Town Beach (11.3 mi / 18.3 km)

Travelling to and around Guilford

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 11.3 mi (18.2 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Bridgeport, CT (BDR-Igor I. Sikorsky Memorial), which is 25.3 mi (40.8 km) away.

If you're travelling by train, you can make your way to Guilford Station.

Frequently asked questions

What is the best area to stay in Guilford when booking a holiday rental?
When seeking the ideal area to stay in Guilford, Connecticut for a holiday rental, the town centre is a fantastic choice. This charming area offers a delightful blend of historic architecture and modern amenities, making it a lovely place to explore. You'll find a variety of properties available, ranging from quaint cottages to more spacious homes, suiting different tastes and budgets.Staying in the town centre puts you within walking distance of key attractions, such as the picturesque Guilford Green, a great spot for leisurely strolls and community events. The nearby Guilford Art Centre also adds a cultural touch, offering classes and exhibitions that showcase local talent. Additionally, the area boasts easy access to the scenic coastline, where you can enjoy beautiful beaches and waterfront activities.Another great option is the neighbourhood surrounding the scenic shoreline, which offers a more tranquil atmosphere. This area features several properties that overlook the water, providing stunning views and a peaceful retreat. Here, you can explore the nearby Hammonasset Beach State Park, known for its expansive sandy beach and nature trails, great for both relaxation and outdoor adventures.
Where are the best areas for renting a beach house in Guilford?
For renting a beach house in Guilford, the scenic shoreline along the Long Island Sound is a prime area to consider. The neighbourhood of Jacobs Beach is particularly appealing, offering direct access to a sandy beach and picturesque views of the water. Many properties in this area come with amenities such as outdoor decks, barbecue facilities, and spacious living areas, superb for families or groups looking to enjoy a coastal retreat.Additionally, the nearby area around the Guilford Town Green provides a charming atmosphere with easy access to local shops and restaurants. Here, you might find historic homes turned into holiday rentals, often featuring characterful interiors, large gardens, and proximity to both the beach and the quaint downtown area.For those who enjoy outdoor activities, the nearby Hammonasset Beach State Park offers expansive sandy beaches and picnic areas, making it an excellent spot for day trips. Rentals in this vicinity typically provide amenities like outdoor seating, beach access, and sometimes even bicycles for exploring the surrounding area.
What is the most popular type of holiday rental accomodation in Guilford?
In Guilford, holiday houses are the most popular type of holiday rental, with about 88 available throughout the area. These properties are typically spacious and well-equipped, featuring multiple bedrooms, large kitchens, and living areas that are great for families or groups. Many also come with outdoor spaces such as gardens or patios, allowing guests to enjoy the scenic surroundings. Additionally, there are around 24 cottages available, which offer a charming, cozy escape with amenities similar to those found in holiday houses. A few cabins and apartments can also be found, providing further variety for travellers looking for a comfortable stay near the picturesque coastline and local attractions.
Are there any family house rentals in Guilford?
In Guilford, Connecticut, there are numerous family-friendly house rentals available, with around 21 options to choose from. This charming coastal town offers a wonderful blend of natural beauty and historical attractions, making it an ideal destination for families. Many of these homes come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for children to play. Amenities such as Wi-Fi and air conditioning are commonly found, ensuring a comfortable stay for all ages.Families can explore nearby points of interest, including the picturesque Guilford Green and the stunning beaches along Long Island Sound. The town is also home to various parks and recreational areas, providing ample opportunities for outdoor activities.
Can I rent a holiday home with a pool or hot tub in Guilford?
In Guilford, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque coastal town offers a charming atmosphere with beautiful scenery and a rich history. Many of the properties come equipped with amenities such as private pools, hot tubs, spacious outdoor areas for relaxation, and fully equipped kitchens, superb for families or groups looking to enjoy a comfortable stay.Travellers can also explore the nearby beaches and enjoy local attractions, including parks and nature reserves.
Are there pet-friendly house rentals in Guilford?
In Guilford, there are several pet-friendly house rentals available, providing an inviting space for travellers with pets. Many of these properties come equipped with comfortable amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.The charming town is known for its picturesque coastal setting, and you'll find holiday rentals that offer easy access to nearby beaches and parks. In particular, the scenic Jacobs Beach is a lovely spot for both humans and pets to enjoy. Additionally, the nearby Guilford Town Green features walking paths and open spaces that are great for leisurely strolls with your furry friends.
Are there any remote work holiday rentals in Guilford?
In Guilford, Connecticut, there are numerous options for remote work holiday rentals, with around 108 available. This picturesque coastal town offers a blend of natural beauty and a quaint New England atmosphere, making it an ideal spot for those looking to work while enjoying a serene environment. Many properties are equipped with reliable Wi-Fi, ensuring connectivity for remote work needs.Travellers can expect a variety of amenities in these rentals, including comfortable workspaces, fully equipped kitchens for convenient meal preparation, and cosy living areas great for relaxation after a day of work. Some accommodations may also feature outdoor spaces, such as patios or gardens, which can provide a refreshing change of scenery during breaks.Guilford's charming downtown area is nearby, where visitors can explore local shops and restaurants, as well as the scenic shoreline with its beautiful beaches and parks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Guilford?
In Guilford, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature outdoor spaces such as decks or patios, great for enjoying the pleasant Connecticut weather. Onsite parking is commonly available, making it convenient for those travelling with a vehicle. Additionally, some rentals may provide amenities like blenders, which can be useful for making smoothies or cocktails.
When is the best time to visit Guilford for a holiday rental?
July is the most popular month to visit Guilford, Connecticut, when the summer season is in full swing. This peak season, stretching from June to August, welcomes visitors seeking a blend of coastal charm and outdoor activities. With pleasant temperatures typically ranging from 20 to 30 degrees Celsius, it's an ideal time for exploring the beautiful beaches, scenic parks, and vibrant local festivals.During July, you can enjoy a lively option, with plenty of opportunities for swimming, hiking, and experiencing the local culture. The warm weather also encourages outdoor dining at charming cafés and restaurants along the picturesque shoreline.For those looking to travel on a budget, December offers a quieter experience with its own unique charm. Although it's the low season, visitors can enjoy the festive holiday decorations and a peaceful ambiance, making it superb for a cozy retreat.Ultimately, choosing the right time to visit Guilford depends on your preference for summer vibrancy or a tranquil winter escape.
What are the top attractions in Guilford?
In Guilford, visitors can enjoy a variety of attractions that highlight the town's charming New England character. The historic Guilford Green is a central hub, surrounded by quaint shops, cafes, and the striking First Congregational Church. Nearby, the Guilford Art Centre offers exhibitions and classes, showcasing local talent and crafts.For nature enthusiasts, the nearby Hammonasset Beach State Park provides beautiful sandy shores and walking trails, great for a day of relaxation or outdoor activities. The Guilford Lakes area features picturesque landscapes, ideal for hiking and enjoying the serene environment.Additionally, the town boasts several historic sites, including the Henry Whitfield State Museum, which is the oldest house in Connecticut, offering insights into the region's historic history.
Are all fees included in the Guilford holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Guilford holiday homes with parking?
Stayz offers a wide selection of holiday homes in Guilford with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Guilford holiday homes?
You can find great discounts on holiday homes in Guilford on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Guilford holiday home booking on Stayz?
To find Guilford holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Guilford?
A long-stay holiday home in Guilford is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Guilford holiday home?
Book your Guilford holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Guilford?
Prices for holiday homes in Guilford vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Guilford to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas