Cambridge holiday rentals

We found 344 holiday rentals — enter your dates for availability
Discover a selection of 91 homes, 14 apartments and other holiday rentals in Cambridge that are perfect for your trip. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as parking and air conditioning. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Cambridge

Showing deals for:18 Dec - 25 Dec

View from Pier back to house!
Pool
Dining table- seats 10!
View from Foyer into Great Room
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

8% off
AU$11,153
for 7 nights, 1 home
AU$1,593 per night
includes taxes & fees
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Pool
The view off of the point, breathtaking.
Interior
Interior
Exceptional
(46 reviews)

Grandview- Main House

Bozman

25% off
AU$6,765
for 7 nights, 1 home
AU$966 per night
includes taxes & fees
Grandview- Main House
Interior
Interior
Exterior
Living area
Excellent
(6 reviews)

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Royal Oak

8% off
AU$12,582
for 7 nights, 1 cottage
AU$1,797 per night
includes taxes & fees
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Custom, open-concept home (photo prior to new red-oak hardwood flooring)
Shaded view of wrap-around deck; stainless Saber outdoor gas grill
"Overlook on Dun's Cove" -- luxury, year-round waterfront vacation rental
Convenient open-concept design: kitchen, dining and living areas
Exceptional
(163 reviews)

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sherwood

10% off
AU$3,389
for 7 nights, 1 home
AU$484 per night
includes taxes & fees
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
two twin beds and play area in loft
Exterior
dining room
view from balcony overlooking playhouse, pergola and Brooks Creek
Exceptional
(276 reviews)

Family and Pet-Friendly, Waterfront with Pier

Cambridge

8% off
AU$3,202
for 7 nights, 1 cottage
AU$457 per night
includes taxes & fees
Family and Pet-Friendly, Waterfront with Pier
Living area
Dining
Private kitchen
Private kitchen
Exceptional
(11 reviews)

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

8% off
AU$4,956
for 7 nights, 1 cottage
AU$708 per night
includes taxes & fees
Charming Waterfront Cottage Retreat near St. Michaels
Property grounds
Exterior
Living area
Dining
Exceptional
(25 reviews)

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman

8% off
AU$4,152
for 7 nights, 1 cottage
AU$593 per night
includes taxes & fees
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Dining Room - Seats 6
View down the lane
Living Room with flat screen TV and sleeper sofa
Sit and stay a while!
Exceptional
(122 reviews)

Perfect Waterview Cottage - St. Michaels Getaway

Wittman

8% off
AU$2,842
for 7 nights, 1 cottage
AU$406 per night
includes taxes & fees
Perfect Waterview Cottage - St. Michaels Getaway
Interior
Private kitchen
Interior
Property grounds
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
AU$6,873
for 7 nights, 1 home
AU$982 per night
includes taxes & fees
Arcadia Shores on the Cove.
Eating Area adjacent Kitchen
Front of W Melson House
Large Screened Porch with rocking chairs
Family Room for reading, playing games, watching television, or just relaxing.
Exceptional
(208 reviews)

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

St. Michaels

8% off
AU$4,458
for 7 nights, 1 cottage
AU$637 per night
includes taxes & fees
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds
Private kitchen
Room
Interior
Exceptional
(10 reviews)

3-bedroom waterfront retreat in Secretary, Maryland

Secretary

8% off
AU$4,808
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
3-bedroom waterfront retreat in Secretary, Maryland
Interior
Be ready to float! Bring your own inner tubes and tennis shoes!
Living area
Living area
Exceptional
(144 reviews)

Charming cottage along water with private pier, near St. Michaels Winery

Bozman

12% off
AU$2,937
for 7 nights, 1 cottage
AU$420 per night
includes taxes & fees
Charming cottage along water with private pier, near St. Michaels Winery
Room
Living area
Living area
Terrace/patio
Exceptional
(7 reviews)

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

St. Michaels

17% off
AU$3,646
for 7 nights, 1 home
AU$521 per night
includes taxes & fees
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
Property grounds
Living area
Private kitchen
Exterior
Exceptional
(414 reviews)

Stay in the HEART of Saint Michaels!

St. Michaels

17% off
AU$2,909
for 7 nights, 1 home
AU$416 per night
includes taxes & fees
Stay in the HEART of Saint Michaels!
Eating area in panelled Family Room. Eat here, in dining room, or on porch!
St. Michaels Harbor from Park down street
Park half block from house
Large screened porch with ceiling fan allows outdoor dining and relaxing.
Exceptional
(150 reviews)

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St. Michaels

8% off
AU$4,115
for 7 nights, 1 cottage
AU$588 per night
includes taxes & fees
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Gather around the table for family dinner.
Every sunrise brings new hope for a brighter future.
Star light, star bright, first star I see tonight.
Life is good!
Exceptional
(52 reviews)

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek

8% off
AU$2,814
for 7 nights, 1 cottage
AU$402 per night
includes taxes & fees
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Living area
Marina
Marina
Private kitchen
Exceptional
(6 reviews)

New, Intown Waterfront Townhome wPool & Location!

Cambridge

10% off
AU$4,260
for 7 nights, 1 home
AU$609 per night
includes taxes & fees
New, Intown Waterfront Townhome wPool & Location!
Property grounds
Outdoor dining
Living area
Dining
Exceptional
(13 reviews)

High Water Guest House<br>

Cambridge

8% off
AU$4,032
for 7 nights, 1 home
AU$576 per night
includes taxes & fees
High Water Guest House<br>
Living Room into Kitchen/Dining
Foyer into Living Room
Kitchen with peak into living room
Foyer with stairs to second floor peak into 1st floor master bedroom
Exceptional
(91 reviews)

Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball

Taylors Island

8% off
AU$6,032
for 7 nights, 1 home
AU$862 per night
includes taxes & fees
Private Waterfront Family Retreat w/ Pier Pool Pickleball Basketball Volleyball
Private kitchen
The beautiful marina is just 4 blocks away
Boutiques and vintage shops are right outside your door
Interior
Exceptional
(11 reviews)

Station House East: Upscale Loft in the Historic District Cambridge, MD

Cambridge

7% off
AU$1,420
for 7 nights, 1 apartment
AU$203 per night
includes taxes & fees
Station House East: Upscale Loft in the Historic District Cambridge, MD
Marina
Marina
Exterior
Property grounds
Exceptional
(13 reviews)

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Cambridge

8% off
AU$2,495
for 7 nights, 1 apartment
AU$356 per night
includes taxes & fees
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Private kitchen
Exterior
Exterior
Living area
Exceptional
(28 reviews)

Spacious waterfront home with amazing views, private pier, fishing and crabbing.

Cambridge

8% off
AU$6,653
for 7 nights, 1 home
AU$950 per night
includes taxes & fees
Spacious waterfront home with amazing views, private pier, fishing and crabbing.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the riverfront beauty of Cambridge

Enjoy the area's museums, architecture and churches with a rental holiday home in Cambridge. This city's bird watching, riverfront and wildlife draw many visitors. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Cambridge

Are you searching for attractions to visit in the city? Venture out of your cosy holiday rental and check out everything that makes Cambridge a fun spot to go on holiday. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (16.6 mi / 26.8 km)
  • Chesapeake Beach Water Park (26.2 mi / 42.1 km)
  • Layton's Chance Vineyard and Winery (10.7 mi / 17.1 km)
  • Bordeleau Winery (27.7 mi / 44.6 km)
  • Bay Country Shop (1.3 mi / 2.1 km)
  • Talbot Massage (14.6 mi / 23.5 km)

Exploring the natural landscape of Cambridge

Travellers enjoy Cambridge for its riverfront and wildlife. Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Cambridge is a great place to get out in nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Long Wharf Park (0.6 mi / 0.9 km)
  • Gerry Boyle Park at Great Marsh (1.1 mi / 1.7 km)
  • Blackwater National Wildlife Refuge (10.4 mi / 16.7 km)
  • Cove Point Beach (21.2 mi / 34 km)
  • Flag Ponds Nature Park (22.4 mi / 36 km)
  • Matoaka Beach (22.7 mi / 36.6 km)

Transport options to and around Cambridge

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 16.8 mi (27 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 34.1 mi (54.8 km) away.

If you're travelling by train, the main station is Cambridge Station.

Frequently asked questions

What is the best area to stay in Cambridge when booking a holiday rental?
When considering a holiday rental in Cambridge, Maryland, the historic district is a popular area to stay. This charming neighbourhood is rich in history and offers a lovely array of beautifully preserved buildings that date back to the 18th and 19th centuries. Visitors can explore the Harriet Tubman Museum and Educational Centre, which highlights the life of the famed abolitionist, and the nearby Choptank River offers picturesque views and opportunities for kayaking and fishing.Another excellent option is the area surrounding Long Wharf Park, where you can enjoy waterfront activities and take leisurely strolls along the scenic boardwalk. This neighbourhood is great for those who appreciate outdoor spaces and local culture, with quaint shops and eateries nearby. The rental properties here tend to reflect the area's rustic charm, providing a comfortable base for exploring all that Cambridge has to offer.
Where are the best areas for renting a beach house in Cambridge?
For renting a beach house in Cambridge, Maryland, the area along the Choptank River and the nearby Chesapeake Bay offers some delightful options. The vicinity of Long Wharf Park is particularly appealing, where visitors can find waterfront properties that boast spectacular views and easy access to the water. Many of these homes come equipped with amenities such as private docks, outdoor decks, and spacious living areas, superb for families or groups looking to enjoy the serene atmosphere of the bay.Further along the river, the neighbourhood of East New Market features charming cottages and larger homes that often include features like fire pits, screened porches, and fully equipped kitchens, making them ideal for self-catering during your stay. This area also provides proximity to local seafood restaurants and quaint shops, adding to the overall experience.Additionally, the nearby Blackwater National Wildlife Refuge offers a unique opportunity for nature lovers, with rentals that may include amenities tailored for outdoor enthusiasts, such as easy access to hiking trails and birdwatching spots. Properties in this area often feature rustic charm, comfortable furnishings, and outdoor spaces for enjoying the peaceful surroundings.
What is the most popular type of holiday rental accomodation in Cambridge?
In Cambridge, holiday houses are the most popular type of holiday rental, with around 292 available throughout the area. These spacious homes often feature multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or gardens, making them ideal for families and larger groups. Additionally, there are about 52 cottages, which provide a charming and rustic atmosphere, great for those looking for a quaint getaway. For a more compact option, approximately 36 apartments and 20 condos can also be found, offering modern amenities and convenient access to local attractions.
Are there any family house rentals in Cambridge?
In Cambridge, Maryland, there are numerous family-friendly house rentals available, with around 70 options throughout the area. Visitors can explore neighbourhoods that offer a mix of coastal charm and historical significance. Many properties feature spacious living areas, well-equipped kitchens superb for family meals, and outdoor spaces ideal for children's play. Amenities like Wi-Fi and air conditioning are typically included to ensure a comfortable stay.Families can take advantage of the town's proximity to nearby attractions such as the Blackwater National Wildlife Refuge, which is great for birdwatching and nature walks, or head to the scenic Choptank River for boating and fishing activities.
Can I rent a holiday home with a pool or hot tub in Cambridge?
In Cambridge, Maryland, there are plenty of holiday homes available for rent that come with pools or hot tubs, with around 38 options to choose from. This charming town, located on the Eastern Shore, offers a variety of waterfront properties along the Choptank River and the nearby Chesapeake Bay. Visitors can find homes in lovely neighbourhoods such as the historic district, which provides a quaint backdrop for a relaxing getaway.Travellers can expect a range of amenities in these rentals, including private swimming pools, hot tubs for unwinding after a day of exploration, and spacious outdoor areas superb for entertaining or enjoying family gatherings.
Are there pet-friendly house rentals in Cambridge?
In Cambridge, Maryland, there are numerous pet-friendly house rentals available, with around 40 options to choose from. Many of these properties come with amenities such as spacious yards, allowing pets to roam freely, as well as fully equipped kitchens and comfortable living spaces for a relaxing stay.The area offers a charming waterfront location along the Choptank River, where visitors can enjoy scenic views and outdoor activities. Nearby parks and nature reserves provide additional opportunities for pet-friendly outings, with walking trails and open spaces superb for exercise and exploration.
Are there any remote work holiday rentals in Cambridge?
In Cambridge, Maryland, there are numerous holiday rentals suitable for remote work, with around 372 options available. Many of these properties come equipped with essential amenities such as free Wi-Fi, dedicated laptop workspaces, and comfortable living areas that provide an ideal setting for productivity. Guests can expect a variety of accommodations, including spacious homes and well-furnished apartments, often featuring fully equipped kitchens and outdoor spaces for relaxation during breaks.The charming town of Cambridge offers a picturesque backdrop, with nearby attractions like the historic waterfront and local parks, great for unwinding after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Cambridge?
In Cambridge, Maryland, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many rentals feature outdoor decks or patios, providing a lovely space to enjoy the fresh air and local scenery. Onsite parking is commonly available, which is particularly convenient for those travelling by car. Additional amenities often include blenders for making smoothies or cocktails and coffee or tea makers, superb for starting the day with a warm beverage.
When is the best time to visit Cambridge for a holiday rental?
The best time to visit Cambridge for a holiday rental is during the summer months, specifically from June to August, when the town comes alive with vibrant activity. This peak season attracts visitors eager to enjoy the beautiful waterfront, partake in outdoor adventures, and explore the local culture. With warm temperatures averaging between 20 to 30 degrees Celsius, it's an ideal time for leisurely strolls along the scenic Choptank River and enjoying water sports like kayaking and paddleboarding.July stands out as the most popular month, offering numerous events and festivals that truly showcase the charm of Cambridge. The lively option invites you to engage with fellow travellers and locals alike, making it a delightful experience for those seeking a fun-filled holiday.If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to appreciate the historic architecture and local shops without the bustling crowds. While the temperatures are cooler, averaging around 10 to 15 degrees Celsius, the town's charm remains intact, providing a peaceful retreat.Ultimately, the best time to book a holiday rental in Cambridge depends on your preference for a bustling summer getaway or a tranquil autumn escape, each offering great experiences to cherish.
What are the top attractions in Cambridge?
In Cambridge, Maryland, visitors can explore several attractions that showcase the area's rich history and natural beauty. The picturesque waterfront offers stunning views and opportunities for boating and fishing, particularly around the Choptank River. Historic sites such as the Harriet Tubman Underground Railroad Museum provide insight into the life and legacy of the iconic abolitionist, and the nearby Blackwater National Wildlife Refuge is superb for nature lovers, featuring trails and birdwatching opportunities.In the downtown area, you'll find charming shops and local eateries that highlight the region's culinary offerings. The Cambridge Main Street area often hosts events and festivals, adding to the vibrant community spirit. For those interested in art and culture, the Dorchester Centre for the Arts frequently showcases local artists and hosts various exhibitions.
Are all fees included in the Cambridge 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 Cambridge holiday homes with parking?
Stayz offers a wide selection of holiday homes in Cambridge 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 Cambridge holiday homes?
You can find great discounts on holiday homes in Cambridge 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 Cambridge holiday home booking on Stayz?
To find Cambridge 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 Cambridge?
A long-stay holiday home in Cambridge 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 Cambridge holiday home?
Book your Cambridge 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 Cambridge?
Prices for holiday homes in Cambridge 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 Cambridge 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.

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