Trumbull Holiday Rentals
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
Kitchen
Air Conditioner
Internet
Child Friendly
US $90/Night
7 Nights - US $632
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
US $216/Night
7 Nights - US $1,514
House
- New Haven
- ·
- Bridgeport
- 1.40 mi to center
1 Bedroom
1 Bath
Oceanfront- Parking
Ocean View
Balcony/Terrace
US $1,130/Night
7 Nights - US $7,911
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
US $399/Night
7 Nights - US $2,795
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
US $576/Night
7 Nights - US $4,035
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $356/Night
7 Nights - US $2,490
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
US $298/Night
7 Nights - US $2,083
Apartment
- New Haven
- ·
- Bridgeport
- 0.74 mi to center
9.8Exceptional
(13 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $231/Night
7 Nights - US $1,617
Apartment
9.8Exceptional
(9 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
Pool- Balcony/Terrace
- Kitchen
US $173/Night
7 Nights - US $1,214
Luxury Holiday Rentals in Trumbull
Over 201+ Luxury Holiday Rentals in or Near Trumbull
House
7 Bedrooms
8 Baths
17 Guests
9999.67 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $2,995/Night
7 Nights - US $20,965
Villa
10.0Exceptional
(6 Reviews)
7 Bedrooms
5 Baths
8 Guests
5700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $2,233/Night
7 Nights - US $15,631
House
6 Bedrooms
5 Baths
11 Guests
3896.54 ft²
Hot Tub- Parking
- Pool
- Balcony/Terrace
US $1,563/Night
7 Nights - US $10,944
House
9.6Exceptional
(5 Reviews)
6 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,473/Night
7 Nights - US $10,311
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
US $1,377/Night
7 Nights - US $9,642
House
8 Bedrooms
5 Baths
17 Guests
6200 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,189/Night
7 Nights - US $8,321
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
US $1,046/Night
7 Nights - US $7,321
House
9.6Exceptional
(4 Reviews)
6 Bedrooms
4 Baths
11 Guests
4000 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $1,037/Night
7 Nights - US $7,261
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
US $1,004/Night
7 Nights - US $7,025
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
(8 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $683/Night
7 Nights - US $4,780
Apartment
9.4Exceptional
(71 Reviews)
1 Bedroom
1 Bath
4 Guests
625 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $184/Night
7 Nights - US $1,291
Hotel
8.8Fabulous
(1009 Reviews)
1 Bath
Breakfast- Parking
- Pool
- Kitchen
US $158/Night
7 Nights - US $1,103
Hotel
8.8Fabulous
(1001 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $185/Night
7 Nights - US $1,294
Hotel
8.6Fabulous
(1000 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $146/Night
7 Nights - US $1,020
Hotel
8.3Excellent
(673 Reviews)
1 Bath
456.39 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
US $283/Night
7 Nights - US $1,978
Hotel
8.0Excellent
(1119 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $136/Night
7 Nights - US $955
Hotel
7.9Very Good
(84 Reviews)
1 Bath
367.05 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $131/Night
7 Nights - US $916
Hotel
7.8Very Good
(1010 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $175/Night
7 Nights - US $1,224
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
US $230/Night
7 Nights - US $1,613
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
US $250/Night
7 Nights - US $1,750
Cottage
1 Bedroom
1 Bath
- Parking
- Ocean View
- Balcony/Terrace
- View
US $652/Night
7 Nights - US $4,563
House
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $203/Night
7 Nights - US $1,419
House
2 Bedrooms
2 Baths
5 Guests
1905.21 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $459/Night
7 Nights - US $3,213
Apartment
- New Haven
- ·
- Bridgeport
- 0.74 mi to center
9.4Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $178/Night
7 Nights - US $1,243
Apartment
- New Haven
- ·
- Bridgeport
- 0.74 mi to center
9.4Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $230/Night
7 Nights - US $1,610
New
House
9.0Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $227/Night
7 Nights - US $1,588
House
8.4Excellent
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
969 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $281/Night
7 Nights - US $1,969
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
US $732/Night
7 Nights - US $5,126
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
US $532/Night
7 Nights - US $3,726
House
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.75 mi to center
9.6Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $465/Night
7 Nights - US $3,256
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
US $614/Night
7 Nights - US $4,299
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
US $761/Night
7 Nights - US $5,324
House
6 Bedrooms
4 Baths
11 Guests
1900 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $929/Night
7 Nights - US $6,502
House
10.0Exceptional
(6 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $689/Night
7 Nights - US $4,822
House
5 Bedrooms
3 Baths
10 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $523/Night
7 Nights - US $3,658
House
- New Haven
- ·
- Bridgeport
- 1.95 mi to center
5 Bedrooms
3 Baths
13 Guests
- Oceanfront
- Ocean View
- View
- Air Conditioner
US $691/Night
7 Nights - US $4,837
Wheelchair Accessible Holiday Homes in Trumbull
Over 6+ Wheelchair Accessible Holiday Homes in or Near Trumbull
Hotel
7.8Very Good
(439 Reviews)
4 Baths
398.26 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $158/Night
7 Nights - US $1,106
Hotel
7.4Very Good
(1004 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $144/Night
7 Nights - US $1,009
Hotel
7.8Very Good
(267 Reviews)
2 Baths
348.03 ft²
- Private Pool
- Oceanfront
- Breakfast
- Pool
US $128/Night
7 Nights - US $893
Hotel
7.8Very Good
(217 Reviews)
1 Bath
637.22 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $154/Night
7 Nights - US $1,079
Hotel
7.2Very Good
(424 Reviews)
5 Baths
301.39 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $129/Night
7 Nights - US $901
Hotel
6.9Good
(262 Reviews)
4 Baths
348.75 ft²
- Private Pool
- Hot Tub
- Breakfast
- Parking
US $162/Night
7 Nights - US $1,132
Trumbull Private Villas and Holiday Homes Under $200
Over 70+ 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
US $196/Night
7 Nights - US $1,369
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
US $186/Night
7 Nights - US $1,301
Hotel
8.0Excellent
(1007 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $181/Night
7 Nights - US $1,269
House
- New Haven
- ·
- West End - West Side
- 0.58 mi to center
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $181/Night
7 Nights - US $1,265
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
US $145/Night
7 Nights - US $1,017
Apartment
1 Bedroom
1 Bath
2 Guests
- Internet
- Pet Friendly
- Child Friendly
Security/Safety
US $180/Night
7 Nights - US $1,260
House
- New Haven
- ·
- Bridgeport
- 1.42 mi to center
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $149/Night
7 Nights - US $1,040
Apartment
1 Bedroom
1 Bath
3 Guests
- Internet
Laundry
Bedding/Linens- Security/Safety
US $98/Night
7 Nights - US $688
New
Apartment
1 Bedroom
1 Bath
2 Guests
- Internet
- Pet Friendly
- Child Friendly
- Laundry
US $195/Night
7 Nights - US $1,362
Instantly Bookable Holiday Homes in Trumbull
Over 82+ 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
US $377/Night
7 Nights - US $2,637
Apartment
- New Haven
- ·
- Bridgeport
- 0.74 mi to center
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $195/Night
7 Nights - US $1,364
House
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.22 mi to center
7.2Very Good
(15 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $268/Night
7 Nights - US $1,873
New
House
- New Haven
- ·
- Bridgeport
- 0.24 mi to center
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $480/Night
7 Nights - US $3,358
Condo
2 Bedrooms
2 Baths
5 Guests
1900 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $382/Night
7 Nights - US $2,671
New
Apartment
- New Haven
- ·
- West End - West Side
- 0.59 mi to center
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $239/Night
7 Nights - US $1,672
Apartment
- New Haven
- ·
- Brooklawn - St. Vincent
- 0.38 mi to center
9.6Exceptional
(26 Reviews)
3 Bedrooms
1 Bath
5 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $389/Night
7 Nights - US $2,722
House
8.0Excellent
(1 Review)
4 Bedrooms
2 Baths
8 Guests
1579 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $579/Night
7 Nights - US $4,056
Apartment
- New Haven
- ·
- Bridgeport
- 0.74 mi to center
6.0Good
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $250/Night
7 Nights - US $1,750
Book a Last Minute Place to Stay in Trumbull
About Casai's Private Villas and Holiday Rentals in Trumbull
Discover more than 210 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 795.61 ft², with nightly prices averaging US $375.
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.
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Top Accommodation Types in Trumbull
| Type | Count |
|---|---|
| Vacation Homes | 95 |
| 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
- MidCenturyMod spectacularly Renovated 1 LEVEL living paradise +EV charger
- Huge Executive Home in Charming Rural Town 1hr NYC
- Cozy studio with 1 bedroom in peaceful Stratford retreat
- Charming &Spacious 3BD, 1BA, Fam-Friendly-Yard&Porch
- Renovated 2BR Retreat/Modern Comforts Included
- Charming 2-bedroom apartment above horse stables on Tuckers Ridge Farm in Easton
- Zen, Spacious & Comfy 2 bed, Lux beds
- Farmhouse from 1800 modernized to feel like home!
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.
- The B&W Haven 3BR private office by LI Ferry
- Cozy Bridgeport Apartment: 2 Mi to Downtown!
How many Casai.com holiday rentals are available in Trumbull?
As of 2026, Casai boasts over 210 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.
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