Trumbull Holiday Rentals
Apartment
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
Kitchen
Air Conditioner
Internet
Child Friendly
CA $115/Night
7 Nights - CA $805
Apartment
- New Haven
- ·
- West End - West Side
- 0.55 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
8 Guests
2002.09 ft²
Parking
View- Air Conditioner
- Internet
CA $298/Night
7 Nights - CA $2,086
House
- New Haven
- ·
- Bridgeport
- 1.40 mi to center
1 Bedroom
1 Bath
Oceanfront- Parking
Ocean View
Balcony/Terrace
CA $2,375/Night
7 Nights - CA $16,628
Apartment
- New Haven
- ·
- West End - West Side
- 0.55 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $550/Night
7 Nights - CA $3,850
Apartment
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.59 mi to center
9.3Exceptional
(4 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Parking
- View
- Air Conditioner
- Internet
CA $794/Night
7 Nights - CA $5,559
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $504/Night
7 Nights - CA $3,527
Apartment
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.42 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
CA $410/Night
7 Nights - CA $2,870
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Internet
- Child Friendly
Laundry
Bedding/Linens
CA $317/Night
7 Nights - CA $2,222
Apartment
- New Haven
- ·
- Bridgeport
- 0.74 mi to center
9.8Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- View
CA $318/Night
7 Nights - CA $2,228
Luxury Holiday Rentals in Trumbull
Over 203+ Luxury Holiday Rentals in or Near Trumbull
House
7 Bedrooms
8 Baths
17 Guests
9999.67 ft²
- Parking
Pool- Air Conditioner
- Internet
CA $4,126/Night
7 Nights - CA $28,882
House
6 Bedrooms
5 Baths
11 Guests
3896.54 ft²
Hot Tub- Parking
- Pool
- Balcony/Terrace
CA $2,154/Night
7 Nights - CA $15,077
House
9.6Exceptional
(5 Reviews)
6 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
CA $2,011/Night
7 Nights - CA $14,081
House
- New Haven
- ·
- Bridgeport
- 1.40 mi to center
8.8Fabulous
(10 Reviews)
6 Bedrooms
3 Baths
15 Guests
3300 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,737/Night
7 Nights - CA $12,159
House
8 Bedrooms
5 Baths
17 Guests
6200 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $1,589/Night
7 Nights - CA $11,123
House
9.6Exceptional
(4 Reviews)
6 Bedrooms
4 Baths
11 Guests
4000 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
CA $1,432/Night
7 Nights - CA $10,026
House
- New Haven
- ·
- Bridgeport
- 1.40 mi to center
8.0Excellent
(1 Review)
6 Bedrooms
4 Baths
15 Guests
3304.52 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
CA $1,383/Night
7 Nights - CA $9,678
House
- Connecticut
- ·
- Monroe
- 0.49 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
3300 ft²
Private Pool- Parking
- Pool
- Ocean View
CA $1,320/Night
7 Nights - CA $9,241
House
6 Bedrooms
4 Baths
11 Guests
1900 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,298/Night
7 Nights - CA $9,084
Top-Rated Holiday Rentals with a Pool in Trumbull
Over 21+ The Best Private Villas and Holiday Rentals in Trumbull with a Pool
House
- Connecticut
- ·
- Redding Ridge
- 1.74 mi to center
10.0Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $1,272/Night
7 Nights - CA $8,905
Apartment
9.8Exceptional
(9 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $259/Night
7 Nights - CA $1,816
Apartment
9.4Exceptional
(72 Reviews)
1 Bedroom
1 Bath
4 Guests
625 ft²
- Private Pool
- Parking
- Pool
- Ocean View
CA $253/Night
7 Nights - CA $1,769
Hotel
8.8Fabulous
(1009 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Kitchen
CA $217/Night
7 Nights - CA $1,520
Hotel
8.8Fabulous
(1004 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
CA $246/Night
7 Nights - CA $1,725
Hotel
8.6Fabulous
(1001 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
CA $228/Night
7 Nights - CA $1,593
Hotel
8.3Excellent
(673 Reviews)
1 Bath
456.39 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
CA $389/Night
7 Nights - CA $2,725
Hotel
8.0Excellent
(1107 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
CA $205/Night
7 Nights - CA $1,433
Hotel
8.0Excellent
(1007 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
CA $394/Night
7 Nights - CA $2,761
Pet-Friendly Holiday Rentals in Trumbull
Over 64+ Pet-Friendly Holiday Rentals in or Near Trumbull
House
- Connecticut
- ·
- Monroe
- 2.55 mi to center
9.6Exceptional
(5 Reviews)
1 Bedroom
1 Bath
3 Guests
550 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $313/Night
7 Nights - CA $2,190
Apartment
- Connecticut
- ·
- Monroe
- 2.80 mi to center
5.5Average
(2 Reviews)
1 Bedroom
1 Bath
3 Guests
5920.15 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
CA $344/Night
7 Nights - CA $2,411
Cottage
1 Bedroom
1 Bath
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $1,033/Night
7 Nights - CA $7,227
House
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- View
CA $287/Night
7 Nights - CA $2,007
House
2 Bedrooms
2 Baths
5 Guests
1905.21 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
CA $632/Night
7 Nights - CA $4,426
Apartment
- New Haven
- ·
- Bridgeport
- 0.74 mi to center
9.4Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- View
CA $320/Night
7 Nights - CA $2,237
House
9.0Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $312/Night
7 Nights - CA $2,188
House
8.4Excellent
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
969 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $460/Night
7 Nights - CA $3,224
Condo
2 Bedrooms
2 Baths
5 Guests
1900 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $590/Night
7 Nights - CA $4,133
Large Holiday Rentals and Private Villas in Trumbull
Over 17+ Large Holiday Rentals and Private Villas in or Near Trumbull
Villa
- New Haven
- ·
- Bridgeport
- 2.56 mi to center
9.6Exceptional
(11 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,013/Night
7 Nights - CA $7,091
House
- New Haven
- ·
- West End - West Side
- 0.55 mi to center
9.6Exceptional
(5 Reviews)
5 Bedrooms
2 Baths
12 Guests
2500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $866/Night
7 Nights - CA $6,060
Apartment
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.30 mi to center
9.4Exceptional
(3 Reviews)
6 Bedrooms
2 Baths
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $846/Night
7 Nights - CA $5,922
House
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.59 mi to center
8.8Fabulous
(10 Reviews)
5 Bedrooms
2 Baths
11 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $1,031/Night
7 Nights - CA $7,219
House
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.75 mi to center
8.4Excellent
(7 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $643/Night
7 Nights - CA $4,499
New
House
- New Haven
- ·
- Bridgeport
- 1.95 mi to center
5 Bedrooms
3 Baths
13 Guests
- Oceanfront
- Ocean View
- View
- Air Conditioner
CA $1,219/Night
7 Nights - CA $8,532
Villa
10.0Exceptional
(6 Reviews)
7 Bedrooms
5 Baths
8 Guests
5700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
CA $3,076/Night
7 Nights - CA $21,534
House
10.0Exceptional
(6 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $949/Night
7 Nights - CA $6,643
House
5 Bedrooms
3 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $720/Night
7 Nights - CA $5,039
Wheelchair Accessible Holiday Homes in Trumbull
Over 7+ Wheelchair Accessible Holiday Homes in or Near Trumbull
Hotel
7.8Very Good
(439 Reviews)
4 Baths
398.26 ft²
- Private Pool
- Breakfast
- Parking
- Pool
CA $218/Night
7 Nights - CA $1,524
Hotel
7.4Very Good
(1014 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
CA $161/Night
7 Nights - CA $1,128
Hotel
7.8Very Good
(267 Reviews)
2 Baths
348.03 ft²
- Private Pool
- Oceanfront
- Breakfast
- Pool
CA $176/Night
7 Nights - CA $1,230
Hotel
7.8Very Good
(217 Reviews)
1 Bath
637.22 ft²
- Private Pool
- Breakfast
- Parking
- Pool
CA $212/Night
7 Nights - CA $1,486
Hotel
7.5Very Good
(84 Reviews)
1 Bath
367.05 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
CA $219/Night
7 Nights - CA $1,536
Hotel
7.2Very Good
(424 Reviews)
5 Baths
301.39 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
CA $177/Night
7 Nights - CA $1,241
Hotel
6.8Good
(264 Reviews)
4 Baths
416.2 ft²
- Private Pool
- Hot Tub
- Breakfast
- Parking
CA $223/Night
7 Nights - CA $1,559
Trumbull Private Villas and Holiday Homes Under $200
Over 69+ Trumbull Private Villas and Holiday Homes Under $200
Apartment
- New Haven
- ·
- Bridgeport
- 0.20 mi to center
2 Bedrooms
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $269/Night
7 Nights - CA $1,886
Apartment
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.59 mi to center
8.9Fabulous
(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- View
- Air Conditioner
- Internet
CA $256/Night
7 Nights - CA $1,792
Hotel
8.0Excellent
(1007 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
CA $250/Night
7 Nights - CA $1,748
New
Apartment
- New Haven
- ·
- Bridgeport
- 1.10 mi to center
2 Bedrooms
2 Baths
4 Guests
1001 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $252/Night
7 Nights - CA $1,765
Apartment
- New Haven
- ·
- West End - West Side
- 0.57 mi to center
8.2Excellent
(9 Reviews)
2 Bedrooms
1 Bath
5 Guests
2002.09 ft²
- Parking
- View
- Air Conditioner
- Internet
CA $200/Night
7 Nights - CA $1,401
New
Apartment
- New Haven
- ·
- Bridgeport
- 1.10 mi to center
2 Bedrooms
2 Baths
4 Guests
1001 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $251/Night
7 Nights - CA $1,759
New
Apartment
- New Haven
- ·
- Bridgeport
- 1.10 mi to center
2 Bedrooms
2 Baths
4 Guests
1001 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $251/Night
7 Nights - CA $1,758
New
Apartment
- New Haven
- ·
- Bridgeport
- 1.10 mi to center
1 Bedroom
1 Bath
2 Guests
667 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $250/Night
7 Nights - CA $1,747
Apartment
1 Bedroom
1 Bath
2 Guests
- Internet
- Pet Friendly
- Child Friendly
Security/Safety
CA $248/Night
7 Nights - CA $1,733
Instantly Bookable Holiday Homes in Trumbull
Over 79+ Instantly Bookable Holiday Homes in or Near Trumbull
Apartment
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.59 mi to center
9.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
2000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $519/Night
7 Nights - CA $3,633
Apartment
- New Haven
- ·
- Bridgeport
- 0.74 mi to center
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- View
CA $268/Night
7 Nights - CA $1,879
House
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.22 mi to center
6.8Good
(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Ocean View
- View
CA $369/Night
7 Nights - CA $2,582
House
- New Haven
- ·
- Bridgeport
- 0.24 mi to center
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
CA $664/Night
7 Nights - CA $4,645
House
- New Haven
- ·
- Bridgeport
- 0.53 mi to center
2 Bedrooms
1 Bath
4 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
CA $474/Night
7 Nights - CA $3,317
Apartment
- New Haven
- ·
- West End - West Side
- 0.59 mi to center
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $329/Night
7 Nights - CA $2,303
New
Apartment
- New Haven
- ·
- Bridgeport
- 1.10 mi to center
1 Bedroom
1 Bath
2 Guests
754 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $229/Night
7 Nights - CA $1,605
New
Apartment
- New Haven
- ·
- Bridgeport
- 1.10 mi to center
1 Bedroom
1 Bath
2 Guests
754 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $224/Night
7 Nights - CA $1,569
Apartment
- New Haven
- ·
- Bridgeport
- 1.10 mi to center
1 Bedroom
1 Bath
2 Guests
754 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
CA $205/Night
7 Nights - CA $1,437
Book a Last Minute Place to Stay in Trumbull
About Casai's Private Villas and Holiday Rentals in Trumbull
Discover more than 212 vacation rentals available in Trumbull. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Trumbull.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Trumbull, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Trumbull. On average, places to stay near Trumbull offer 788.42 ft², with nightly prices averaging CA $530.
With Casai, finding and comparing holiday rentals in Trumbull is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Trumbull
| Type | Count |
|---|---|
| Vacation Homes | 97 |
| Holiday Apartments | 92 |
| Cottages | 2 |
| Villas | 2 |
Use these Quick Filters to Find a Holiday Rental in Trumbull
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Trumbull.
Weather in Trumbull, CT
View the weather forecast for Trumbull before booking your Trumbull Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Trumbull, CT
Casai offers a large selection of top attractions around Trumbull . Research things to do on your vacation before you visit Trumbull.
Other Places to Stay in Trumbull, CT
Frequently Asked Questions About Trumbull?
What are the top holiday rentals in Trumbull?
With numerous options available in Trumbull, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Trumbull:
- Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train
- Quiet suburban home close to Fairfield beaches and universities
- Soothing Carriage House with Hot Tub in charming Stratford
- MidCenturyMod spectacularly Renovated 1 LEVEL living paradise +EV charger
- Cozy studio with 1 bedroom in peaceful Stratford retreat
- Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
- Renovated 2BR Retreat/Modern Comforts Included
- Cozy 1 br apartment with a private entrance and patio in Fairfield
- Charming 2-bedroom apartment above horse stables on Tuckers Ridge Farm in Easton
- Zen, Spacious & Comfy 2 bed, Lux beds
How many holiday rentals have private pools in Trumbull?
Discover a selection of holiday rentals with private pools near Trumbull with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- 🌟 Fairfield Luxury Estate for Short or Mid Term Stays | 🏊 Pool | 🎾 Tennis | 🧖 Sauna
- Peaceful, cheerful 4 bedroom home with a pool
- Winter Wonderland
Which holiday homes in Trumbull are best for families?
If you're searching for a family-friendly holiday home in Trumbull, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Trumbull:
- My little place Cozy Open concept for quiet time.
- 4 Mi to Beach & Dtwn! Charming Fairfield Home
- Linwood Whole House
How many Casai.ca holiday rentals are available in Trumbull?
As of 2026, Casai boasts over 212 properties listed in the Trumbull area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Trumbull.
Map
