Cambridge, MD Vacation Rentals

Our Favorite Vacation Rentals in Cambridge

  • Cambridge Colonial Home, Walk to Town & Waterfront
     3br Home/Apartment
    HolidayLettings
    From
    $485
  • Waterfront Vacation Home with Private Beach
     3br Home/Apartment
    HolidayLettings
    From
    $395
  • Stunning, Newer Chesapeake Waterfront Estate, Pool - 6/7 Bedrms 5 Baths
    Good6br Home/Apartment
    Flipkey
    From
    $1,048
  • Sailwinds Loft at Cambridge Creek
    Excellent2br Home/Apartment
    Airbnb
    From
    $119
  • Riverview House
    Excellent2br Home/Apartment
    Airbnb
    From
    $308
  • BLACKWATER CHARM FAMILY HOUSE
    Excellent6br Home/Apartment
    Airbnb
    From
    $194
  • The Spinnaker At Swan Cove Manor
    Excellent5br Home/Apartment
    Airbnb
    From
    $1,017
  • Home by the Choptank River
    Excellent3br Home/Apartment
    Airbnb
    From
    $291

Check prices for these upcoming dates

Cambridge Vacation Rentals with a Pool

  • Chesapeake Sunset Cottage
    Excellent2br Home/Apartment
    Airbnb
    From
    $350
  • Comfy Cambridge cottage with sandy beach and pool
     Cottage
    Airbnb
    From
    $311
  • Gorgeous Waterfront Estate w/Pool- 6/7 Bdrms - 5ba
    Excellent7br Home/Apartment
    Airbnb
    From
    $959
  • The Mariner at Swan Cove Manor
     5br Home/Apartment
    Airbnb
    From
    $1,017

Cambridge Vacation Rentals with Wi-Fi

  • Pleasant Place
     3br Home/Apartment
    Airbnb
    From
    $1,130
  • Charming Country Retreat
     3br Home/Apartment
    Airbnb
    From
    $353
  • FALL getaway Waterfront -Kayaks - Sleeps 13- VIEW!
    Excellent5br Home/Apartment
    Airbnb
    From
    $537
  • Cambridge Waterfront Rancher
    Excellent4br Home/Apartment
    Airbnb
    From
    $593

Cambridge Pet-Friendly Vacation Rentals

  • Private, waterfront farmhouse
    Excellent5br Farmhouse
    Airbnb
    From
    $607
  • Church Creek Nature's Rest
    ExcellentHome/Apartment
    Airbnb
    From
    $113
  • Apt located near Downtown/Wildlife Refuge/Ironman
     Home/Apartment
    Airbnb
    From
    $89
  • Camper & Club house
    Excellent2br Home/Apartment
    Airbnb
    From
    $254

Cambridge Travel Guide

Cambridge, a charming Dorchester County city, sits beside the Choptank River. It’s the fourth biggest city in the Eastern Shore region and boasts a rich maritime history that is celebrated throughout the year. Despite having a relatively small number of permanent residents, Cambridge is a must see on the bucket list of many travelers.

Things to Do in Cambridge

Like many ocean side cities, Cambridge offers a variety of unique outdoor activities. To get the vacation started, many visitors make it a point to go sailing on the Skipjack Nathan of Dorchester- a 60+ foot skipjack that offers sailors the chance to catch oysters, crabs, and other small creatures from the boat's deck, as well as to learn about the history of Cambridge. Long Wharf Park, on the other hand, offers a unique experience from Cambridge’s shores- visitors can bring a blanket and picnic basket and spend the day relaxing on the pier, watching the boats come in, and marveling over the old fisherman-style homes in the area. The Choptank River Lighthouse is a great night destination, while the Blackwater National Wildlife Refuge is better suited for day trips and visitors who value wildlife. Bringing things indoors, the Harriet Tubman Museum and Educational Center enlightens curious visitors about the life and slavery relief efforts of Harriet Tubman and the UGRR (underground railroad) by way of carefully designed exhibits and stories. The Richardson Maritime Museum, Sago Spa & Salon, and the Christ Episcopal Church are also locations worthy of mention.

Best Places to Stay in Cambridge

The rental homes in Cambridge are known within the area for their scenic water views and small-town, rustic charm. Most of them include a large living room, full bathroom, and up to three bedrooms with comfortable beds and updated appliances throughout the house.

Best Time to Visit Cambridge

The best time to visit Cambridge is from June to September when the summer weather is at its peak.

Food in Cambridge

For a taste of authentic Italian food, Carmela’s Cucina is the go-to restaurant in Cambridge. Jimmie and Sooks, offering American fare and seafood, is another popular casual place to eat, while The Bay Country Bakery & Cafe satisfies even the biggest of sweet tooth with its donuts, pastries, and cakes.

Best Events in Cambridge

Cambridge’s annual Seafood Feastival brings seafood lovers of all ages to the city to enjoy an event filled with all-you-can-eat crab, shrimp, crab soup, clams, and oysters. The Santa Swim is an annual event that raises money for those in need in Dorchester. The event has residents dressing up in festive costumes and rewards swimmers with refreshments. Other events worth noting are the Summer Sendoff, Christmas Parade, and Eagleman Triathalon.

Price and Availability in Cambridge

Most expensive
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The cheapest day to stay at a vacation rental in Cambridge tends to be Sunday, while the most expensive day tends to be Wednesday. Vacation homes in Cambridge tend to be busiest on Thursdays, while it tends to be much quieter on Mondays.
The most expensive month to stay in a vacation rental in Cambridge is in March, while the cheapest month is in August. The most popular time to book a vacation rental in Cambridge is in the high season in June. Cambridge has its low season in January, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Cambridge

Rainy days
73° 23°
7
64° 23°
4
68°
3
75° 18°
4
73° 25°
2
81° 30°
3
88° 43°
11
91° 54°
2
95° 52°
7
91° 57°
1
91° 59°
5
88° 34°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Cambridge. The hottest month in Cambridge is June, when temperatures peak at 95 ˚F. The coolest month is December, when temperatures drop to 1 ˚F. The wettest month in Cambridge is August with 10.53 inches of rain, while the driest month is May with 0.5 inches of rain.

What Expert Travelers Think

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  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

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  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

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Vacation Rentals in Cambridge

At AllTheRooms.com we have vacation rentals from all of the best providers - Airbnb, Priceline, Bed and Breakfast and more. We have 405 vacation rentals, hotels and other places to stay in Cambridge ranging from cheap options to luxury places to stay. If you are wanting to keep costs down, the cheapest place to stay in Cambridge is only $40 per night. An average vacation rental in Cambridge costs on average $368 a night.

Those looking to get some work finished during their trip to Cambridge can choose from 224 places to stay that provide WiFi. 54 places to stay include a morning meal. Choose from 6 places to stay that provide gym options, so you don't miss a single workout. If you're planning on getting to Cambridge by car, be sure to choose from 234 accommodations that provide parking. 37 hotels and vacation rentals have a a pool or jacuzzi

If you're traveling with a furry friend, then make sure to choose one of the 54 pet-friendly accommodations available.

274 of the accommodations in Cambridge have been rated by previous guests. They rated 59% as excellent or good. 141 accommodations allow instant booking.

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